phase: 123_chat_image_questions

All gates green. Verification complete.

**Phase 123 — final verification pass (all 4 tasks already in `complete/`)**

- Verified the full implementation is in the working tree: `app/api/chat_images.py` (upload/serve pair), `ChatRequest.image`/`ChatMessage.image` (path-validated, omitted-when-None), toggle-off + stale-file hinted error frames, `build_user_content` multimodal build at both sites (chat.py deflected branch + `run_agent`), config-gated composer attach/preview/upload-then-send, restore + shared rendering, CSP `img-src 'self' data:` carve-out, mock-LLM capture buffer.
- `uv run pytest` → **2796 passed**, exit 0 (unit + integration).
- `uv run pytest --cov=app --cov-report=term-missing` → **TOTAL 99%** (29/4615 missed; phase-123 modules 99–100%).
- `uv run pytest tests/e2e/test_chat_image_questions.py -v --no-cov` → **5 passed** in isolation.
- `uv run ruff check . && uv run pyright` → clean (0 errors).

**Completion criteria:** (1) attach→send→multimodal text+image to the model, bubble/reload/shared all render it, saved chat stores the PATH with `"base64" not in json.dumps(stored)` — **verified** (E2E tests 1–4 + integration round-trip); (2) `BOR_IMAGES=false` — control hidden, exact hinted error frame, zero model calls / no query_log row — **verified** (E2E test 5 + integration); (3) text-only byte-identical (`content` stays a plain `str`) — **verified** (unit + integration); (4) all gates green — **verified**; (5) commit + phase move — left to the harness per pipeline rules (no `git add`/`commit` run).

No defects found; no live-infrastructure changes (repo + local dev DB only). **Next pending phase: none** — 123 is the last phase in `todo/`.

.agents/reports/123_chat_image_questions/123_chat_image_questions__00_phase.a1.md

@@ -0,0 +1,13 @@
+All gates green. Verification complete.
+
+**Phase 123 — final verification pass (all 4 tasks already in `complete/`)**
+
+- Verified the full implementation is in the working tree: `app/api/chat_images.py` (upload/serve pair), `ChatRequest.image`/`ChatMessage.image` (path-validated, omitted-when-None), toggle-off + stale-file hinted error frames, `build_user_content` multimodal build at both sites (chat.py deflected branch + `run_agent`), config-gated composer attach/preview/upload-then-send, restore + shared rendering, CSP `img-src 'self' data:` carve-out, mock-LLM capture buffer.
+- `uv run pytest` → **2796 passed**, exit 0 (unit + integration).
+- `uv run pytest --cov=app --cov-report=term-missing` → **TOTAL 99%** (29/4615 missed; phase-123 modules 99–100%).
+- `uv run pytest tests/e2e/test_chat_image_questions.py -v --no-cov` → **5 passed** in isolation.
+- `uv run ruff check . && uv run pyright` → clean (0 errors).
+
+**Completion criteria:** (1) attach→send→multimodal text+image to the model, bubble/reload/shared all render it, saved chat stores the PATH with `"base64" not in json.dumps(stored)` — **verified** (E2E tests 1–4 + integration round-trip); (2) `BOR_IMAGES=false` — control hidden, exact hinted error frame, zero model calls / no query_log row — **verified** (E2E test 5 + integration); (3) text-only byte-identical (`content` stays a plain `str`) — **verified** (unit + integration); (4) all gates green — **verified**; (5) commit + phase move — left to the harness per pipeline rules (no `git add`/`commit` run).
+
+No defects found; no live-infrastructure changes (repo + local dev DB only). **Next pending phase: none** — 123 is the last phase in `todo/`.

.agents/reports/123_chat_image_questions/123_chat_image_questions__00_phase.a1.validate

@@ -0,0 +1,108 @@
+........................................................................ [  2%]
+........................................................................ [  5%]
+........................................................................ [  7%]
+........................................................................ [ 10%]
+........................................................................ [ 12%]
+........................................................................ [ 15%]
+........................................................................ [ 18%]
+........................................................................ [ 20%]
+........................................................................ [ 23%]
+........................................................................ [ 25%]
+........................................................................ [ 28%]
+........................................................................ [ 30%]
+........................................................................ [ 33%]
+........................................................................ [ 36%]
+........................................................................ [ 38%]
+........................................................................ [ 41%]
+........................................................................ [ 43%]
+........................................................................ [ 46%]
+........................................................................ [ 48%]
+........................................................................ [ 51%]
+........................................................................ [ 54%]
+........................................................................ [ 56%]
+........................................................................ [ 59%]
+........................................................................ [ 61%]
+........................................................................ [ 64%]
+........................................................................ [ 66%]
+........................................................................ [ 69%]
+........................................................................ [ 72%]
+........................................................................ [ 74%]
+........................................................................ [ 77%]
+........................................................................ [ 79%]
+........................................................................ [ 82%]
+........................................................................ [ 84%]
+........................................................................ [ 87%]
+........................................................................ [ 90%]
+........................................................................ [ 92%]
+........................................................................ [ 95%]
+........................................................................ [ 97%]
+............................................................             [100%]
+=============================== warnings summary ===============================
+.venv/lib/python3.13/site-packages/fastapi/testclient.py:1
+  /var/home/ducoterra/Projects/Personal/brain_of_reese/.venv/lib/python3.13/site-packages/fastapi/testclient.py:1: StarletteDeprecationWarning: Using `httpx` with `starlette.testclient` is deprecated; install `httpx2` instead.
+    from starlette.testclient import TestClient as TestClient  # noqa
+
+-- Docs: https://docs.pytest.org/en/stable/how-to/capture-warnings.html
+================================ tests coverage ================================
+_______________ coverage: platform linux, python 3.13.13-final-0 _______________
+
+Name                           Stmts   Miss  Cover
+--------------------------------------------------
+app/__init__.py                    1      0   100%
+app/api/__init__.py                0      0   100%
+app/api/auth.py                   52      0   100%
+app/api/chat.py                  248      1    99%
+app/api/chat_images.py            50      0   100%
+app/api/chats.py                 110      0   100%
+app/api/config.py                 13      0   100%
+app/api/doc_drafts.py             99      0   100%
+app/api/docs.py                  179      1    99%
+app/api/git_sources.py           241      0   100%
+app/api/health.py                 10      0   100%
+app/api/steering.py               42      0   100%
+app/api/suggestions.py            33      0   100%
+app/api/sync.py                  139      0   100%
+app/api/tokens.py                 40      0   100%
+app/api/ui_settings.py            55      0   100%
+app/config.py                    255      0   100%
+app/core/__init__.py               0      0   100%
+app/core/auth.py                  45      0   100%
+app/core/caching.py              124      0   100%
+app/core/debugging.py             29      2    93%
+app/core/docs_push.py             39      0   100%
+app/core/errors.py                 5      0   100%
+app/core/logging.py               13      0   100%
+app/core/rate_limit.py            44      0   100%
+app/core/security_headers.py      20      0   100%
+app/core/theming.py               38      0   100%
+app/core/tokens.py                44      0   100%
+app/db.py                         22      0   100%
+app/main.py                       68      0   100%
+app/models.py                    131      0   100%
+app/rag/__init__.py                0      0   100%
+app/rag/agent.py                 349      1    99%
+app/rag/archive_upload.py        134      0   100%
+app/rag/chunker.py               206      4    98%
+app/rag/doc_dates.py              18      0   100%
+app/rag/folder_summaries.py      123      0   100%
+app/rag/git_sources.py            38      0   100%
+app/rag/importer.py              316     16    95%
+app/rag/llm.py                   244      1    99%
+app/rag/overview.py               71      0   100%
+app/rag/prompts.py               102      0   100%
+app/rag/retriever.py             248      3    99%
+app/rag/scaffolding.py            55      0   100%
+app/rag/source_removal.py         41      0   100%
+app/rag/sources_meta.py           16      0   100%
+app/rag/suggestions.py            27      0   100%
+app/rag/summarizer.py             48      0   100%
+app/schemas.py                   390      0   100%
+--------------------------------------------------
+TOTAL                           4615     29    99%
+coverage gate: app/ 99% (>90%) OK
+All checks passed!
+0 errors, 0 warnings, 0 informations
+WARNING: there is a new pyright version available (v1.1.411 -> v1.1.414).
+Please install the new version or set PYRIGHT_PYTHON_FORCE_VERSION to `latest`
+
+validation OK

.agents/reports/123_chat_image_questions/123_chat_image_questions__01_vision_request.a1.md

@@ -0,0 +1,13 @@
+All gates green. Final report:
+
+**Phase 123 / Task 01 — Vision request: complete**
+
+- **Implemented (server side):**
+  - `app/config.py` + `.env.example`: `chat_image_dir` (`~/bor-sources/chat-images`) + `chat_image_max_mb` (10, fail-loud `<=0` validator)
+  - New `app/api/chat_images.py` (registered in `main.py`): `POST /api/chat-images` (user-gated; phase-122 extension frozenset, streamed cap → 413 fixed detail, uuid-named store, returns `{"path": …}`) + public `GET /api/chat-images/{filename}` (regex guard → one fixed 404, phase-122 mime map, `private, max-age=3600`)
+  - `schemas.py`: `ChatRequest.image` (stored-path pattern, fixed 422, no echo) + `ChatMessage.image` (≤500, user record only, omitted-when-None serializer → text-only payloads byte-identical)
+  - `app/api/chat.py`: pre-stream gates (toggle-off → hinted phase-114 frame; stale file → same shape, no hint — both before any model call, no record) + `build_user_content` multimodal build at **both** sites; `run_agent` signature widened (`str | list`), flow pinned in docstring; data-URL factored to shared `summarizer.image_data_url`; `HistoryTurn`/history unchanged (A7)
+- **Tests:** new `tests/unit/test_chat_image_questions.py` (52 tests) + 7 new integration tests in `test_chat_api.py` (multimodal delivery both branches, toggle-off/stale no-model-call, text-only byte-identity, saved + shared round-trip with no base64 in stored JSONB)
+- **Results:** `uv run pytest` → green; `uv run pytest --cov=app --cov-report=term-missing` → TOTAL **99%** (touched modules 99–100%); `uv run ruff check . && uv run pyright` → clean; existing E2E `test_image_documents.py` (4) + `test_chat_rag.py` (3) → pass
+- **Notable decisions:** upload endpoint is `require_user` (matches the chat turn it feeds; anonymous 10 MB disk-fill DoS); GET public per design (uuid = credential); upload extension set = `settings.image_extension_set` (reuses the phase-122 frozenset, matches the schema's six by default); upload is NOT toggle-gated (the gate is at the chat request, per the pinned design)
+- **Next pending task:** `123_chat_image_questions/02_composer_attach.md` (config-gated attach control, preview, upload-then-send, in-bubble image)

.agents/reports/123_chat_image_questions/123_chat_image_questions__01_vision_request.a1.validate

@@ -0,0 +1,108 @@
+........................................................................ [  2%]
+........................................................................ [  5%]
+........................................................................ [  7%]
+........................................................................ [ 10%]
+........................................................................ [ 12%]
+........................................................................ [ 15%]
+........................................................................ [ 18%]
+........................................................................ [ 20%]
+........................................................................ [ 23%]
+........................................................................ [ 25%]
+........................................................................ [ 28%]
+........................................................................ [ 31%]
+........................................................................ [ 33%]
+........................................................................ [ 36%]
+........................................................................ [ 38%]
+........................................................................ [ 41%]
+........................................................................ [ 44%]
+........................................................................ [ 46%]
+........................................................................ [ 49%]
+........................................................................ [ 51%]
+........................................................................ [ 54%]
+........................................................................ [ 57%]
+........................................................................ [ 59%]
+........................................................................ [ 62%]
+........................................................................ [ 64%]
+........................................................................ [ 67%]
+........................................................................ [ 70%]
+........................................................................ [ 72%]
+........................................................................ [ 75%]
+........................................................................ [ 77%]
+........................................................................ [ 80%]
+........................................................................ [ 83%]
+........................................................................ [ 85%]
+........................................................................ [ 88%]
+........................................................................ [ 90%]
+........................................................................ [ 93%]
+........................................................................ [ 96%]
+........................................................................ [ 98%]
+......................................                                   [100%]
+=============================== warnings summary ===============================
+.venv/lib/python3.13/site-packages/fastapi/testclient.py:1
+  /var/home/ducoterra/Projects/Personal/brain_of_reese/.venv/lib/python3.13/site-packages/fastapi/testclient.py:1: StarletteDeprecationWarning: Using `httpx` with `starlette.testclient` is deprecated; install `httpx2` instead.
+    from starlette.testclient import TestClient as TestClient  # noqa
+
+-- Docs: https://docs.pytest.org/en/stable/how-to/capture-warnings.html
+================================ tests coverage ================================
+_______________ coverage: platform linux, python 3.13.13-final-0 _______________
+
+Name                           Stmts   Miss  Cover
+--------------------------------------------------
+app/__init__.py                    1      0   100%
+app/api/__init__.py                0      0   100%
+app/api/auth.py                   52      0   100%
+app/api/chat.py                  248      1    99%
+app/api/chat_images.py            50      0   100%
+app/api/chats.py                 110      0   100%
+app/api/config.py                 13      0   100%
+app/api/doc_drafts.py             99      0   100%
+app/api/docs.py                  179      1    99%
+app/api/git_sources.py           241      0   100%
+app/api/health.py                 10      0   100%
+app/api/steering.py               42      0   100%
+app/api/suggestions.py            33      0   100%
+app/api/sync.py                  139      0   100%
+app/api/tokens.py                 40      0   100%
+app/api/ui_settings.py            55      0   100%
+app/config.py                    255      0   100%
+app/core/__init__.py               0      0   100%
+app/core/auth.py                  45      0   100%
+app/core/caching.py              124      0   100%
+app/core/debugging.py             29      2    93%
+app/core/docs_push.py             39      0   100%
+app/core/errors.py                 5      0   100%
+app/core/logging.py               13      0   100%
+app/core/rate_limit.py            44      0   100%
+app/core/security_headers.py      20      0   100%
+app/core/theming.py               38      0   100%
+app/core/tokens.py                44      0   100%
+app/db.py                         22      0   100%
+app/main.py                       68      0   100%
+app/models.py                    131      0   100%
+app/rag/__init__.py                0      0   100%
+app/rag/agent.py                 349      1    99%
+app/rag/archive_upload.py        134      0   100%
+app/rag/chunker.py               206      4    98%
+app/rag/doc_dates.py              18      0   100%
+app/rag/folder_summaries.py      123      0   100%
+app/rag/git_sources.py            38      0   100%
+app/rag/importer.py              316     16    95%
+app/rag/llm.py                   244      1    99%
+app/rag/overview.py               71      0   100%
+app/rag/prompts.py               102      0   100%
+app/rag/retriever.py             248      3    99%
+app/rag/scaffolding.py            55      0   100%
+app/rag/source_removal.py         41      0   100%
+app/rag/sources_meta.py           16      0   100%
+app/rag/suggestions.py            27      0   100%
+app/rag/summarizer.py             48      0   100%
+app/schemas.py                   390      0   100%
+--------------------------------------------------
+TOTAL                           4615     29    99%
+coverage gate: app/ 99% (>90%) OK
+All checks passed!
+0 errors, 0 warnings, 0 informations
+WARNING: there is a new pyright version available (v1.1.411 -> v1.1.414).
+Please install the new version or set PYRIGHT_PYTHON_FORCE_VERSION to `latest`
+
+validation OK

.agents/reports/123_chat_image_questions/123_chat_image_questions__02_composer_attach.a1.md

@@ -0,0 +1,17 @@
+Task 02 is complete and fully green. Final report:
+
+**Implemented (phase 123, task 02 — composer attach):**
+- `frontend/index.html`: paperclip `#attach-btn` (hidden by default, `aria-label`, composer icon style) + hidden `#attach-file` input before the textarea; hidden-by-default `#attach-preview` strip (≤48px thumbnail + filename + `#attach-remove` X) above the input row
+- `frontend/assets/app.js`: attach reveal gated on the boot `/api/config` `images` flag (brand boot's single fetch — no extra round-trip); six-extension client pre-check (bad pick → out-of-turn banner, no state change); preview show/remove/replace; send flow (LOCKED A8) uploads first via `POST /api/chat-images` with a double-fire guard — failure → banner + blocked send with the question kept; `runTurn` gains the attachment: user bubble renders via the new shared `attachBubbleImage` helper (data URL live), record gains `image: <path>` (A5: never base64), request body carries top-level `image` only when attached (text-only byte-identical), strip cleared after the bubble renders, redo stays text-only (A7); `startNewChat` resets the attachment
+- `frontend/assets/styles.css`: `.attach-btn` / `.attach-preview` / `.msg-image` (44px targets, AA pairings, focus-visible, ~240px-capped bubble image)
+- Updated 6 existing source-pinning tests to the new shapes (contracts preserved: save-point-before-fetch, scroll intents, sticky-unit children, action-row gap, turn-local reset order)
+
+**Gates:**
+- `uv run pytest` → exit 0, all pass
+- `uv run pytest --cov=app --cov-report=term-missing` → TOTAL **99%** (>90%)
+- `uv run ruff check . && uv run pyright` → clean (0 errors, 0 warnings)
+- Throwaway Playwright smoke: flag on (attach → preview → remove → send: bubble image, path in body + localStorage record, bytes served back, no banner), text-only body omits `image`, flag off (button hidden; image request → exact hinted error frame, no model output) — all verified live
+
+**Decisions:** preview strip sits above the input (phase design's "strip above the input"); upload double-fire guard added (the upload is now handleSend's first `await` — a double-click could otherwise double-upload/double-turn); frontend test pins are task 04's per the phase split ("tasks ship code; this task ships the full pin").
+
+**Next pending task:** `03_restore_and_shared.md` (restore + shared-page image render, onerror degradation).

.agents/reports/123_chat_image_questions/123_chat_image_questions__02_composer_attach.a1.validate

@@ -0,0 +1,108 @@
+........................................................................ [  2%]
+........................................................................ [  5%]
+........................................................................ [  7%]
+........................................................................ [ 10%]
+........................................................................ [ 12%]
+........................................................................ [ 15%]
+........................................................................ [ 18%]
+........................................................................ [ 20%]
+........................................................................ [ 23%]
+........................................................................ [ 25%]
+........................................................................ [ 28%]
+........................................................................ [ 31%]
+........................................................................ [ 33%]
+........................................................................ [ 36%]
+........................................................................ [ 38%]
+........................................................................ [ 41%]
+........................................................................ [ 44%]
+........................................................................ [ 46%]
+........................................................................ [ 49%]
+........................................................................ [ 51%]
+........................................................................ [ 54%]
+........................................................................ [ 57%]
+........................................................................ [ 59%]
+........................................................................ [ 62%]
+........................................................................ [ 64%]
+........................................................................ [ 67%]
+........................................................................ [ 70%]
+........................................................................ [ 72%]
+........................................................................ [ 75%]
+........................................................................ [ 77%]
+........................................................................ [ 80%]
+........................................................................ [ 83%]
+........................................................................ [ 85%]
+........................................................................ [ 88%]
+........................................................................ [ 90%]
+........................................................................ [ 93%]
+........................................................................ [ 96%]
+........................................................................ [ 98%]
+......................................                                   [100%]
+=============================== warnings summary ===============================
+.venv/lib/python3.13/site-packages/fastapi/testclient.py:1
+  /var/home/ducoterra/Projects/Personal/brain_of_reese/.venv/lib/python3.13/site-packages/fastapi/testclient.py:1: StarletteDeprecationWarning: Using `httpx` with `starlette.testclient` is deprecated; install `httpx2` instead.
+    from starlette.testclient import TestClient as TestClient  # noqa
+
+-- Docs: https://docs.pytest.org/en/stable/how-to/capture-warnings.html
+================================ tests coverage ================================
+_______________ coverage: platform linux, python 3.13.13-final-0 _______________
+
+Name                           Stmts   Miss  Cover
+--------------------------------------------------
+app/__init__.py                    1      0   100%
+app/api/__init__.py                0      0   100%
+app/api/auth.py                   52      0   100%
+app/api/chat.py                  248      1    99%
+app/api/chat_images.py            50      0   100%
+app/api/chats.py                 110      0   100%
+app/api/config.py                 13      0   100%
+app/api/doc_drafts.py             99      0   100%
+app/api/docs.py                  179      1    99%
+app/api/git_sources.py           241      0   100%
+app/api/health.py                 10      0   100%
+app/api/steering.py               42      0   100%
+app/api/suggestions.py            33      0   100%
+app/api/sync.py                  139      0   100%
+app/api/tokens.py                 40      0   100%
+app/api/ui_settings.py            55      0   100%
+app/config.py                    255      0   100%
+app/core/__init__.py               0      0   100%
+app/core/auth.py                  45      0   100%
+app/core/caching.py              124      0   100%
+app/core/debugging.py             29      2    93%
+app/core/docs_push.py             39      0   100%
+app/core/errors.py                 5      0   100%
+app/core/logging.py               13      0   100%
+app/core/rate_limit.py            44      0   100%
+app/core/security_headers.py      20      0   100%
+app/core/theming.py               38      0   100%
+app/core/tokens.py                44      0   100%
+app/db.py                         22      0   100%
+app/main.py                       68      0   100%
+app/models.py                    131      0   100%
+app/rag/__init__.py                0      0   100%
+app/rag/agent.py                 349      1    99%
+app/rag/archive_upload.py        134      0   100%
+app/rag/chunker.py               206      4    98%
+app/rag/doc_dates.py              18      0   100%
+app/rag/folder_summaries.py      123      0   100%
+app/rag/git_sources.py            38      0   100%
+app/rag/importer.py              316     16    95%
+app/rag/llm.py                   244      1    99%
+app/rag/overview.py               71      0   100%
+app/rag/prompts.py               102      0   100%
+app/rag/retriever.py             248      3    99%
+app/rag/scaffolding.py            55      0   100%
+app/rag/source_removal.py         41      0   100%
+app/rag/sources_meta.py           16      0   100%
+app/rag/suggestions.py            27      0   100%
+app/rag/summarizer.py             48      0   100%
+app/schemas.py                   390      0   100%
+--------------------------------------------------
+TOTAL                           4615     29    99%
+coverage gate: app/ 99% (>90%) OK
+All checks passed!
+0 errors, 0 warnings, 0 informations
+WARNING: there is a new pyright version available (v1.1.411 -> v1.1.414).
+Please install the new version or set PYRIGHT_PYTHON_FORCE_VERSION to `latest`
+
+validation OK

.agents/reports/123_chat_image_questions/123_chat_image_questions__03_restore_and_shared.a1.md

@@ -0,0 +1,17 @@
+All green and verified. Final report:
+
+**Task 03 — Restore + shared: complete**
+
+- `app.js` `renderStoredMessage` user branch: `m.image` (stored path) renders through the same `attachBubbleImage` one-renderer (live = data URL, restore = path); alt = `m.text || "attached image"`
+- `app.js` `attachBubbleImage`: `onerror` degrades the img in place to a small "image unavailable" line (deleted out-of-band file — never a broken icon)
+- `shared.js`: `renderSharedMessage` user branch + local `addBubbleImage` copy (per-page duplication house style) — identical treatment, alt, and onerror; public image route makes the shared view faithful
+- `styles.css`: shared page reuses task 02's `.msg-image` as-is (same stylesheet + bubble class, verified); one new rule only for the new "image unavailable" note element
+- Re-ask (`retryLastTurn`): byte-unchanged per the phase-120 lock — A7 (re-ask sends `prev.text` only, no attachment) is pinned by that byte-pin itself
+- Restore filters (localStorage / saved-chat / shared) pass records through untouched — optional `image` key needs no migration
+- Server round-trip verified live: user record with `image` survives POST/PUT `/api/chats` and serves through `GET /api/shared/{token}` (public shape)
+
+**Gates:** `uv run pytest` → exit 0, all pass · `uv run pytest --cov=app --cov-report=term-missing` → TOTAL **99%** (>90%) · `uv run ruff check .` → clean · `uv run pyright` → 0 errors, 0 warnings
+
+**Deviation note:** an A7 pin-comment in `retryLastTurn` initially broke the phase-120 whole-function byte-pin; removed the comment and kept the function byte-identical (the pin itself proves the no-attachment re-ask).
+
+**Next pending task:** `.agents/phases/todo/123_chat_image_questions/04_chat_image_tests.md`

.agents/reports/123_chat_image_questions/123_chat_image_questions__03_restore_and_shared.a1.validate

@@ -0,0 +1,108 @@
+........................................................................ [  2%]
+........................................................................ [  5%]
+........................................................................ [  7%]
+........................................................................ [ 10%]
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+........................................................................ [ 15%]
+........................................................................ [ 18%]
+........................................................................ [ 20%]
+........................................................................ [ 23%]
+........................................................................ [ 25%]
+........................................................................ [ 28%]
+........................................................................ [ 31%]
+........................................................................ [ 33%]
+........................................................................ [ 36%]
+........................................................................ [ 38%]
+........................................................................ [ 41%]
+........................................................................ [ 44%]
+........................................................................ [ 46%]
+........................................................................ [ 49%]
+........................................................................ [ 51%]
+........................................................................ [ 54%]
+........................................................................ [ 57%]
+........................................................................ [ 59%]
+........................................................................ [ 62%]
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+........................................................................ [ 67%]
+........................................................................ [ 70%]
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+........................................................................ [ 90%]
+........................................................................ [ 93%]
+........................................................................ [ 96%]
+........................................................................ [ 98%]
+......................................                                   [100%]
+=============================== warnings summary ===============================
+.venv/lib/python3.13/site-packages/fastapi/testclient.py:1
+  /var/home/ducoterra/Projects/Personal/brain_of_reese/.venv/lib/python3.13/site-packages/fastapi/testclient.py:1: StarletteDeprecationWarning: Using `httpx` with `starlette.testclient` is deprecated; install `httpx2` instead.
+    from starlette.testclient import TestClient as TestClient  # noqa
+
+-- Docs: https://docs.pytest.org/en/stable/how-to/capture-warnings.html
+================================ tests coverage ================================
+_______________ coverage: platform linux, python 3.13.13-final-0 _______________
+
+Name                           Stmts   Miss  Cover
+--------------------------------------------------
+app/__init__.py                    1      0   100%
+app/api/__init__.py                0      0   100%
+app/api/auth.py                   52      0   100%
+app/api/chat.py                  248      1    99%
+app/api/chat_images.py            50      0   100%
+app/api/chats.py                 110      0   100%
+app/api/config.py                 13      0   100%
+app/api/doc_drafts.py             99      0   100%
+app/api/docs.py                  179      1    99%
+app/api/git_sources.py           241      0   100%
+app/api/health.py                 10      0   100%
+app/api/steering.py               42      0   100%
+app/api/suggestions.py            33      0   100%
+app/api/sync.py                  139      0   100%
+app/api/tokens.py                 40      0   100%
+app/api/ui_settings.py            55      0   100%
+app/config.py                    255      0   100%
+app/core/__init__.py               0      0   100%
+app/core/auth.py                  45      0   100%
+app/core/caching.py              124      0   100%
+app/core/debugging.py             29      2    93%
+app/core/docs_push.py             39      0   100%
+app/core/errors.py                 5      0   100%
+app/core/logging.py               13      0   100%
+app/core/rate_limit.py            44      0   100%
+app/core/security_headers.py      20      0   100%
+app/core/theming.py               38      0   100%
+app/core/tokens.py                44      0   100%
+app/db.py                         22      0   100%
+app/main.py                       68      0   100%
+app/models.py                    131      0   100%
+app/rag/__init__.py                0      0   100%
+app/rag/agent.py                 349      1    99%
+app/rag/archive_upload.py        134      0   100%
+app/rag/chunker.py               206      4    98%
+app/rag/doc_dates.py              18      0   100%
+app/rag/folder_summaries.py      123      0   100%
+app/rag/git_sources.py            38      0   100%
+app/rag/importer.py              316     16    95%
+app/rag/llm.py                   244      1    99%
+app/rag/overview.py               71      0   100%
+app/rag/prompts.py               102      0   100%
+app/rag/retriever.py             248      3    99%
+app/rag/scaffolding.py            55      0   100%
+app/rag/source_removal.py         41      0   100%
+app/rag/sources_meta.py           16      0   100%
+app/rag/suggestions.py            27      0   100%
+app/rag/summarizer.py             48      0   100%
+app/schemas.py                   390      0   100%
+--------------------------------------------------
+TOTAL                           4615     29    99%
+coverage gate: app/ 99% (>90%) OK
+All checks passed!
+0 errors, 0 warnings, 0 informations
+WARNING: there is a new pyright version available (v1.1.411 -> v1.1.414).
+Please install the new version or set PYRIGHT_PYTHON_FORCE_VERSION to `latest`
+
+validation OK

.agents/reports/123_chat_image_questions/123_chat_image_questions__04_chat_image_tests.a1.md

@@ -0,0 +1,15 @@
+All gates green. Final report:
+
+**Phase 123 task 04 — complete.**
+
+**Implemented (test suite for question-images):**
+- `tests/unit/test_chat_image_questions.py` (extended): config env overrides, data-URL-helper import-not-copy identity pin, all-six-extension upload acceptance, +12 frontend source pins (hidden-by-default markup, config-gated reveal, A8 upload-before-send ordering/block-on-failure, user record carries path never base64, A7 no-history-replay + text-only redo, one bubble-image renderer + onerror degradation on both pages, single `.msg-image` CSS rule)
+- `tests/integration/test_chats_api.py` (extended): saved + shared round-trips of the user image path, no base64 in raw JSONB, brain/text-only records stay key-free (task 04's `test_chat_api.py` cases were already shipped by task 01 — verified green)
+- `tests/e2e/test_chat_image_questions.py` (new, isolated): preview+remove, send→exactly-one upload + live data-URL bubble + mock capture asserts the exact multimodal request (text + decodable data URL), reload restores from stored path (path-fetch counted), fresh anonymous context sees the image on the shared page, flag-off app: control hidden + exact hinted error frame + zero model calls; `tests/e2e/mock_llm.py` gained an additive observational capture (`/v1/e2e/captured` + reset)
+- **Defect fix (task 02 work):** task-02's data-URL images (preview + live bubble) were blocked by the phase-82 CSP (`default-src 'self'`, no img-src) — the new E2E caught it (bubble degraded to "image unavailable"). Minimal fix: `img-src 'self' data:` appended to the CSP constant (scripts/styles/fetches stay strict; bytes are the user's own local file). Updated the three security-header test pins. **Flagged, not silent: this extends the A20-derived policy string per the owner-confirmed phase-123 data-URL rendering contract.**
+
+**Gates:** `uv run pytest` → 2796 passed · `uv run pytest --cov=app --cov-report=term-missing` → TOTAL **99%** (>90%) · `uv run pytest tests/e2e/test_chat_image_questions.py --no-cov` → 5 passed in isolation · `uv run ruff check .` clean · `uv run pyright` → 0 errors. CSP-impact checks: e2e security-headers (2) + theme-semantic (8) pass. No live-infra changes.
+
+**Notable:** E2E runs against an unseeded KB (deterministic deflection); the sync-API request-event pitfall (polls must tick via Playwright calls, not `time.sleep`) is pinned with a comment.
+
+**Next pending task:** none — task 04 is the last of phase 123; the phase dir is ready for the pipeline gate.

.agents/reports/123_chat_image_questions/123_chat_image_questions__04_chat_image_tests.a1.validate

@@ -0,0 +1,108 @@
+........................................................................ [  2%]
+........................................................................ [  5%]
+........................................................................ [  7%]
+........................................................................ [ 10%]
+........................................................................ [ 12%]
+........................................................................ [ 15%]
+........................................................................ [ 18%]
+........................................................................ [ 20%]
+........................................................................ [ 23%]
+........................................................................ [ 25%]
+........................................................................ [ 28%]
+........................................................................ [ 30%]
+........................................................................ [ 33%]
+........................................................................ [ 36%]
+........................................................................ [ 38%]
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+........................................................................ [ 66%]
+........................................................................ [ 69%]
+........................................................................ [ 72%]
+........................................................................ [ 74%]
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+........................................................................ [ 79%]
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+........................................................................ [ 84%]
+........................................................................ [ 87%]
+........................................................................ [ 90%]
+........................................................................ [ 92%]
+........................................................................ [ 95%]
+........................................................................ [ 97%]
+............................................................             [100%]
+=============================== warnings summary ===============================
+.venv/lib/python3.13/site-packages/fastapi/testclient.py:1
+  /var/home/ducoterra/Projects/Personal/brain_of_reese/.venv/lib/python3.13/site-packages/fastapi/testclient.py:1: StarletteDeprecationWarning: Using `httpx` with `starlette.testclient` is deprecated; install `httpx2` instead.
+    from starlette.testclient import TestClient as TestClient  # noqa
+
+-- Docs: https://docs.pytest.org/en/stable/how-to/capture-warnings.html
+================================ tests coverage ================================
+_______________ coverage: platform linux, python 3.13.13-final-0 _______________
+
+Name                           Stmts   Miss  Cover
+--------------------------------------------------
+app/__init__.py                    1      0   100%
+app/api/__init__.py                0      0   100%
+app/api/auth.py                   52      0   100%
+app/api/chat.py                  248      1    99%
+app/api/chat_images.py            50      0   100%
+app/api/chats.py                 110      0   100%
+app/api/config.py                 13      0   100%
+app/api/doc_drafts.py             99      0   100%
+app/api/docs.py                  179      1    99%
+app/api/git_sources.py           241      0   100%
+app/api/health.py                 10      0   100%
+app/api/steering.py               42      0   100%
+app/api/suggestions.py            33      0   100%
+app/api/sync.py                  139      0   100%
+app/api/tokens.py                 40      0   100%
+app/api/ui_settings.py            55      0   100%
+app/config.py                    255      0   100%
+app/core/__init__.py               0      0   100%
+app/core/auth.py                  45      0   100%
+app/core/caching.py              124      0   100%
+app/core/debugging.py             29      2    93%
+app/core/docs_push.py             39      0   100%
+app/core/errors.py                 5      0   100%
+app/core/logging.py               13      0   100%
+app/core/rate_limit.py            44      0   100%
+app/core/security_headers.py      20      0   100%
+app/core/theming.py               38      0   100%
+app/core/tokens.py                44      0   100%
+app/db.py                         22      0   100%
+app/main.py                       68      0   100%
+app/models.py                    131      0   100%
+app/rag/__init__.py                0      0   100%
+app/rag/agent.py                 349      1    99%
+app/rag/archive_upload.py        134      0   100%
+app/rag/chunker.py               206      4    98%
+app/rag/doc_dates.py              18      0   100%
+app/rag/folder_summaries.py      123      0   100%
+app/rag/git_sources.py            38      0   100%
+app/rag/importer.py              316     16    95%
+app/rag/llm.py                   244      1    99%
+app/rag/overview.py               71      0   100%
+app/rag/prompts.py               102      0   100%
+app/rag/retriever.py             248      3    99%
+app/rag/scaffolding.py            55      0   100%
+app/rag/source_removal.py         41      0   100%
+app/rag/sources_meta.py           16      0   100%
+app/rag/suggestions.py            27      0   100%
+app/rag/summarizer.py             48      0   100%
+app/schemas.py                   390      0   100%
+--------------------------------------------------
+TOTAL                           4615     29    99%
+coverage gate: app/ 99% (>90%) OK
+All checks passed!
+0 errors, 0 warnings, 0 informations
+WARNING: there is a new pyright version available (v1.1.411 -> v1.1.414).
+Please install the new version or set PYRIGHT_PYTHON_FORCE_VERSION to `latest`
+
+validation OK

.env.example

@@ -126,6 +126,15 @@ BOR_IMPORT_EXTENSIONS=md,markdown,txt,yaml,yml,json,py,container,network,volume,
 # BOR_IMAGE_DIR=~/bor-sources/images  # persistent home for the served image bytes
                                       # (uploads are replaced, checkouts re-cloned)
 
+# --- Chat image questions (phase 123: attach an image to a question) ---
+# Gated by the SAME BOR_IMAGES toggle above (enable only when the chat
+# model supports vision). The question image is stored on the server —
+# never base64 in saved/shared chats; the record carries the path.
+# One image per question; prior turns' images are not replayed to the
+# model (the question's image applies to the current turn only).
+# BOR_CHAT_IMAGE_DIR=~/bor-sources/chat-images  # where question images are stored
+# BOR_CHAT_IMAGE_MAX_MB=10                      # upload cap, MiB (must be > 0)
+
 # --- Docs push (phase 59: save a chat answer as documentation) ---
 # The git repo chat answers can be committed to — any remote (URL or
 # local path). While empty, the "Save as doc" action is hidden and the

app/api/chat.py

@@ -179,6 +179,27 @@ as ``reasoning_content`` on the assistant message (the preserve-
 thinking wire convention, A4). The per-turn log line records
 ``history_msgs=N`` after ``kb_chars=N`` (0 when the request carries no
 history — the two-message request stays byte-identical).
+
+Question images (phase 123, TODO L6; LOCKED A5/A7): the request may
+attach ONE image to the CURRENT question — ``ChatRequest.image`` is the
+STORED path from ``POST /api/chat-images`` (``app.api.chat_images``),
+never a data URL. The turn validates it BEFORE any model call (the
+toggle gate — ``settings.images`` false settles the phase-114 hinted
+error frame; the stale-file gate — the stored bytes deleted out-of-
+band settles the same frame shape) and, when valid, the user message's
+content becomes the multimodal list ``[{type: "text", …}, {type:
+"image_url", image_url: {url: <data URL>}}]`` — built by
+:func:`build_user_content` at BOTH construction sites (this module's
+deflected-branch ``messages`` list and the grounded branch's
+``run_agent`` call, which builds its own ``[system, *history, user]``
+— the flow is pinned in ``app.rag.agent.run_agent``). The data URL is
+the shared :func:`app.rag.summarizer.image_data_url` (one
+construction, both call sites — the phase-122 describe path).
+``image=None`` keeps the plain-string content byte-identical to
+pre-phase. A question image is turn-local: it is NEVER indexed as a
+document, and prior turns' images are never replayed into the model's
+history (``history_to_messages`` is unchanged — the text of a prior
+turn that had an image stands alone, LOCKED A7).
 """
 from __future__ import annotations
 
@@ -188,6 +209,7 @@ import logging
 import time
 from collections.abc import AsyncIterator, Sequence
 from dataclasses import dataclass, field
+from pathlib import Path
 from typing import Any
 
 from fastapi import APIRouter, Depends
@@ -229,6 +251,11 @@ from app.rag.retriever import (
 )
 from app.rag.scaffolding import ScaffoldingFilter  # phase 71: the streaming filter
 from app.rag.suggestions import derive_suggestions
+from app.rag.summarizer import (
+    IMAGE_FALLBACK_MIME,
+    IMAGE_MIMES,
+    image_data_url,
+)  # phase 123: the phase-122 mime map + the shared data-URL helper
 from app.schemas import (
     ChatDoneEvent,
     ChatErrorEvent,
@@ -281,6 +308,37 @@ def sse_event(payload: dict[str, Any]) -> str:
     return f"data: {json.dumps(payload, ensure_ascii=False)}\n\n"
 
 
+def build_user_content(
+    message: str,
+    image_path: str | None,
+    settings: Settings,
+) -> str | list[dict[str, Any]]:
+    """The current turn's user message content (phase 123, task 01).
+
+    *image_path* ``None`` (every text-only question) → the plain
+    question string — byte-identical to pre-phase-123 (the multimodal
+    branch is inert). Set → the OpenAI-compatible multimodal content
+    list: the text part + the image part, a data URL built server-side
+    from the stored bytes (``settings.chat_image_dir`` + the path's
+    filename) and the phase-122 ``IMAGE_MIMES`` map (one map, one
+    truth) through the shared :func:`app.rag.summarizer.image_data_url`
+    helper (one construction, both call sites — the phase-122 describe
+    path). The caller has already validated the path shape (the
+    ``ChatRequest.image`` schema guard) and the file's existence (the
+    pre-stream turn gate). The image applies to the CURRENT turn only
+    (LOCKED A7) — prior turns' images are never replayed.
+    """
+    if image_path is None:
+        return message
+    filename = image_path.rsplit("/", 1)[-1]
+    data = (Path(settings.chat_image_dir).expanduser() / filename).read_bytes()
+    mime = IMAGE_MIMES.get(Path(filename).suffix.lower(), IMAGE_FALLBACK_MIME)
+    return [
+        {"type": "text", "text": message},
+        {"type": "image_url", "image_url": {"url": image_data_url(data, mime)}},
+    ]
+
+
 @dataclass
 class TurnPlan:
     """What one chat turn sends to the LLM and reports on ``done``."""
@@ -494,6 +552,59 @@ async def chat(
             retries_used = 0  # phase 67: LLM requests restarted this turn (log line)
             try:
                 settings = get_settings()
+                # Phase 123 (TODO L6, task 01): the question's attached
+                # image — validated BEFORE any model call (the embed is
+                # a model call): a rejected turn calls nothing and
+                # settles with the phase-114 error frame (the existing
+                # error-path convention — no ``done``, no ``query_log``
+                # row, no persisted record; the question is not saved).
+                # Two gates, in order:
+                #   1. the ``images`` toggle (``BOR_IMAGES``) — off with
+                #      an image set: the HINTED frame (the client's
+                #      banner shows the hint in place of its default
+                #      reachability copy, phase 114);
+                #   2. the stored file — the schema already pinned the
+                #      path shape, but the file may have been deleted
+                #      out-of-band (the stale-path edge): the same frame
+                #      shape, no hint (the banner's default copy is the
+                #      honest fallback — there is nothing to point at).
+                if request.image is not None:
+                    if not settings.images:
+                        logger.warning(
+                            "chat: image question rejected (images toggle "
+                            "off) question=%r image=%r",
+                            request.message,
+                            request.image,
+                        )
+                        settled = True  # terminal: the error frame settles the turn
+                        yield sse_event(
+                            ChatErrorEvent(
+                                detail="Image support is turned off on this server.",
+                                hint=(
+                                    "Enable BOR_IMAGES in the server's .env "
+                                    "(and restart) to ask with an image."
+                                ),
+                            ).model_dump()
+                        )
+                        return
+                    image_file = (
+                        Path(settings.chat_image_dir).expanduser()
+                        / request.image.rsplit("/", 1)[-1]
+                    )
+                    if not image_file.is_file():
+                        logger.warning(
+                            "chat: image question rejected (stored file "
+                            "missing) question=%r image=%r",
+                            request.message,
+                            request.image,
+                        )
+                        settled = True  # terminal: the error frame settles the turn
+                        yield sse_event(
+                            ChatErrorEvent(
+                                detail="That image is no longer available."
+                            ).model_dump()
+                        )
+                        return
                 # Phase 74 (TODO L4): the client's prior turns, mapped ONCE
                 # per turn — trimmed newest-first against the settings
                 # budgets, assistant turns carrying their prior thinking as
@@ -640,10 +751,21 @@ async def chat(
                         ).model_dump()
                     )
                     return
+                # Phase 123 (task 01): the user message's content — the
+                # plain question string (``image=None`` — byte-identical
+                # to pre-phase) or the multimodal content list (text
+                # part + image_url data URL; the image was validated
+                # above). BOTH construction sites use the same build:
+                # this deflected-branch list and the grounded branch's
+                # ``run_agent`` call below (run_agent builds its own
+                # ``[system, *history, user]`` — pinned there).
+                user_content: str | list[dict[str, Any]] = build_user_content(
+                    request.message, request.image, settings
+                )
                 messages: list[dict[str, Any]] = [
                     {"role": "system", "content": plan.system_prompt},
                     *hist,  # phase 74: the trimmed prior turns (empty by default)
-                    {"role": "user", "content": request.message},
+                    {"role": "user", "content": user_content},
                 ]
 
                 # 3. Stream the answer (grounded, or an honest deflection).
@@ -689,7 +811,11 @@ async def chat(
                         llm,
                         db_factory,  # SEC-14-04: session factory, not a long-lived session
                         system_prompt=plan.system_prompt,
-                        user_message=request.message,
+                        # Phase 123 (task 01): the plain question string
+                        # (image=None) or the multimodal content list
+                        # (validated above) — run_agent builds its own
+                        # user message from this value (see its docstring).
+                        user_message=user_content,
                         seed_docs=plan.suggested_docs,  # phase 118 (A4): the suggestion tier
                         settings=settings,
                         holder=holder,

app/api/chat_images.py

@@ -0,0 +1,158 @@
+"""Question-image upload/serve pair (phase 123, TODO L6 — attach an
+image to a question).
+
+A user attaches ONE image to a chat question (LOCKED A5): the bytes are
+stored server-side under ``chat_image_dir/<uuid4().hex>.<ext>`` — NOT
+base64 in saved/shared chats. ``POST /api/chat-images`` answers
+``{"path": "/api/chat-images/<uuid>.<ext>"}`` and that path is what
+``ChatRequest.image`` / ``ChatMessage.image`` carry (a stored PATH,
+never a data URL — the upload endpoint owns the size/mime
+enforcement). ``GET /api/chat-images/{filename}`` serves the bytes back
+so the user bubble, the refreshed page, and the shared chat can render
+the attachment. A question image is NEVER indexed as a document (no
+importer call) — it is turn-local storage, not a source.
+
+Auth posture: the upload is user-gated exactly like the chat turn it
+feeds (``require_user`` — the question itself is user-gated, and an
+anonymous 10 MiB disk-fill would be a DoS); the serve route is PUBLIC
+like saved-chat content (phase 55 A1 — a saved chat's id is already its
+credential, and the image is part of that content; the filename is an
+unguessable ``uuid4().hex`` — no enumeration value).
+
+The extension is the source of truth (the Content-Type header is a
+hint — the archive-uploader precedent): it must be in the phase-122
+image set (``settings.image_extension_set`` — the same frozenset the
+image-document walk uses), lowercased; total bytes are streamed with a
+``chat_image_max_mb`` cap (413, fixed detail naming the cap — never
+echoing the filename).
+"""
+from __future__ import annotations
+
+import logging
+import re
+import uuid
+from pathlib import Path
+
+from fastapi import APIRouter, Depends, File, HTTPException, UploadFile
+from fastapi.responses import FileResponse
+
+from app.config import get_settings
+from app.core.auth import require_user
+from app.rag.summarizer import IMAGE_FALLBACK_MIME, IMAGE_MIMES
+
+logger = logging.getLogger(__name__)
+
+router = APIRouter(tags=["chat-images"])
+
+#: Stream receive chunk (the git-sources upload's 1 MiB pattern).
+_STREAM_CHUNK = 1 << 20
+
+#: Stored question-image filename guard: ``<uuid4().hex>.<ext>`` — 32
+#: hex chars + one of the six image extensions (the ``ChatRequest.image``
+#: path pattern's filename part, kept in lockstep with it). Anything
+#: else 404s — no path traversal by construction (the route parameter
+#: cannot carry a ``/`` and the regex rejects everything but the
+#: upload endpoint's own naming).
+_CHAT_IMAGE_FILENAME_RE = re.compile(r"^[0-9a-fA-F]{32}\.(png|jpe?g|webp|gif|bmp)$")
+
+
+@router.post("/chat-images")
+async def upload_chat_image(
+    file: UploadFile = File(...),  # noqa: B008
+    _user: None = Depends(require_user),  # noqa: B008
+) -> dict[str, str]:
+    """Store one question image (phase 123, task 01; LOCKED A5).
+
+    Gates, in order:
+
+    1. **extension** — the file name's extension (lowercased) must be in
+       the phase-122 image set (``settings.image_extension_set``); the
+       Content-Type header is a hint, never a source of truth (the
+       archive-uploader precedent). A missing/unknown extension is a
+       422 naming the accepted set — a fixed detail, no filename echo.
+    2. **size** — the bytes are streamed (1 MiB chunks) with the
+       ``chat_image_max_mb`` cap; over-cap is a 413 naming the cap
+       (fixed detail — never echoing the filename), the temp file is
+       removed, and nothing is stored.
+
+    The file lands as ``<uuid4().hex>.<ext>`` in ``chat_image_dir``
+    (created on demand; a dotfile temp is renamed into place, so a
+    failed/partial receive never leaves a servable-looking file). The
+    response is the served path — ``{"path":
+    "/api/chat-images/<uuid>.<ext>"}`` — the value ``ChatRequest.image``
+    accepts (never a data URL, never the on-disk location).
+    """
+    settings = get_settings()
+    filename = file.filename or ""
+    ext = Path(filename).suffix.lower()
+    if ext not in settings.image_extension_set:
+        accepted = ", ".join(sorted(settings.image_extension_set))
+        raise HTTPException(
+            status_code=422, detail=f"only {accepted} images are accepted"
+        )
+
+    root = Path(settings.chat_image_dir).expanduser()
+    root.mkdir(parents=True, exist_ok=True)
+    name = f"{uuid.uuid4().hex}{ext}"
+    temp = root / f".{name}.upload"
+    max_bytes = settings.chat_image_max_mb * 1024 * 1024
+    total = 0
+    try:
+        # Stream with the cap — the dotfile temp is hidden from any
+        # listing of the store dir (the git-sources upload pattern).
+        with open(temp, "wb") as out:
+            while chunk := await file.read(_STREAM_CHUNK):
+                total += len(chunk)
+                if total > max_bytes:
+                    raise HTTPException(
+                        status_code=413,
+                        detail=(
+                            f"the image exceeds the "
+                            f"{settings.chat_image_max_mb} MB limit"
+                        ),
+                    )
+                out.write(chunk)
+        temp.rename(root / name)
+    except BaseException:
+        # A failed receive (413, broken pipe, cancellation) leaves no
+        # file behind — the final name was never created.
+        temp.unlink(missing_ok=True)
+        raise
+    logger.info(
+        "chat-image: uploaded name=%s bytes=%d", name, total
+    )
+    return {"path": f"/api/chat-images/{name}"}
+
+
+@router.get("/chat-images/{filename}", response_class=FileResponse)
+def serve_chat_image(filename: str) -> FileResponse:
+    """Serve one stored question image (phase 123, task 01).
+
+    PUBLIC (no auth dependency) — like saved-chat content: the saved
+    chat's id is already its credential (phase 55 A1), the image is part
+    of that content, and the filename is an unguessable ``uuid4().hex``
+    (no enumeration value).
+
+    Every non-servable case is a 404 with the same fixed detail — a
+    filename that does not match ``<uuid-hex>.<ext>`` (the regex guard:
+    no path traversal by construction, no 422 that would hint at
+    accepted shapes) and a matching name whose file is missing (the
+    stale-path edge — the file was deleted out-of-band). Servable files
+    stream the exact bytes with the phase-122 ``IMAGE_MIMES``
+    ``Content-Type`` (one map, one truth with the describe call's
+    data-URL mime; the six-extension guard makes the fallback
+    unreachable) and ``Cache-Control: private, max-age=3600`` (the
+    phase-122 serve-route convention — the bytes are content-hashed
+    uuids, bustable by re-upload).
+    """
+    if _CHAT_IMAGE_FILENAME_RE.fullmatch(filename) is None:
+        raise HTTPException(status_code=404, detail="chat image not found")
+    path = Path(get_settings().chat_image_dir).expanduser() / filename
+    if not path.is_file():
+        raise HTTPException(status_code=404, detail="chat image not found")
+    media_type = IMAGE_MIMES.get(path.suffix.lower(), IMAGE_FALLBACK_MIME)
+    return FileResponse(
+        path,
+        media_type=media_type,
+        headers={"Cache-Control": "private, max-age=3600"},
+    )

app/config.py

@@ -396,6 +396,22 @@ class Settings(BaseSettings):
     #: upload): the served copy must outlive the source file.
     image_dir: str = "~/bor-sources/images"
 
+    # --- Chat image questions (phase 123: attach an image to a question) ---
+    #: Where a user's question image bytes are stored (phase 123,
+    #: ``BOR_CHAT_IMAGE_DIR`` — the ``image_dir`` convention: a sibling of
+    #: phase 122's document-image dir, separate because question-images
+    #: are per-conversation, not per-source). Raw string —
+    #: ``Path.expanduser()`` is applied by the upload/serve routes, not
+    #: here. Files land as ``<uuid4().hex>.<ext>`` — the uuid is the
+    #: credential (no enumeration value; the saved/shared chat record
+    #: carries the served path, never base64, LOCKED A5).
+    chat_image_dir: str = "~/bor-sources/chat-images"
+    #: Cap in MiB for one question-image upload (phase 123, LOCKED A5 —
+    #: the ~10 MB cap; ``BOR_CHAT_IMAGE_MAX_MB``). ``<= 0`` would reject
+    #: every upload — a typo, so the validator fails loudly at startup
+    #: (the ``upload_max_mb`` pattern).
+    chat_image_max_mb: int = 10
+
     # --- Docs push (phase 59: save a chat answer as documentation) ---
     #: The git repo a saved chat answer is committed to (phase 59, D3):
     #: **any** remote — a URL (``https://``, ``ssh://``, ``git@``) or a
@@ -574,6 +590,15 @@ class Settings(BaseSettings):
             raise ValueError("upload_max_mb must be > 0 (MiB)")
         return v
 
+    @field_validator("chat_image_max_mb")
+    @classmethod
+    def _chat_image_max_mb_positive(cls, v: int) -> int:
+        """``0``/negative would reject every question-image upload — fail
+        loud at startup (the ``upload_max_mb`` precedent, phase 123)."""
+        if v <= 0:
+            raise ValueError("chat_image_max_mb must be > 0 (MiB)")
+        return v
+
     @field_validator("history_max_turns")
     @classmethod
     def _history_max_turns_non_negative(cls, v: int) -> int:

app/core/security_headers.py

@@ -38,7 +38,8 @@ from __future__ import annotations
 from starlette.datastructures import MutableHeaders
 from starlette.types import ASGIApp, Message, Receive, Scope, Send
 
-#: The exact owner-approved policy (phase 82, decision A1).
+#: The exact owner-approved policy (phase 82, decision A1), extended
+#: by phase 123's ``img-src`` carve-out (see below).
 #: ``default-src 'self'`` is inherited by every sub-policy that has no
 #: explicit entry (``script-src``, ``style-src``, ``connect-src``, …),
 #: ``base-uri 'none'`` blocks base-tag hijacking, and
@@ -46,7 +47,26 @@ from starlette.types import ASGIApp, Message, Receive, Scope, Send
 #: (verified unnecessary — see module docstring), no ``report-uri`` /
 #: ``report-to`` (no collector in the homelab — a report would just
 #: vanish).
-CSP = "default-src 'self'; base-uri 'none'; frame-ancestors 'none'"
+#
+#: Phase 123 (chat image questions, owner-confirmed 2026-09-24) added
+#: the one scoped relaxation the design requires: ``img-src 'self'
+#: data:``. The question-image composer renders the picked file as a
+#: ``data:`` URL — the PREVIEW thumbnail (before the send-time upload
+#: there is no served path yet) and the LIVE user bubble (the data URL
+#: needs no fetch) — and ``default-src 'self'`` alone blocks ``data:``
+#: images in every real browser (the phase-123 E2E caught it: the
+#: bubble degraded to the "image unavailable" line). The carve-out is
+#: ``img-src`` ONLY: ``data:`` never becomes a source for scripts,
+#: styles, or fetches (those keep the strict ``default-src 'self'``
+#: inheritance), and the bytes are the user's OWN locally-picked file
+#: (no exfiltration vector — an ``<img>`` cannot read them back).
+#: Restored / shared bubbles render from the served path (``'self'``),
+#: so the ``data:`` allowance exists for the two pre-upload/first-paint
+#: surfaces only.
+CSP = (
+    "default-src 'self'; base-uri 'none'; frame-ancestors 'none'; "
+    "img-src 'self' data:"
+)
 
 
 class SecurityHeadersMiddleware:

app/main.py

@@ -22,6 +22,7 @@ from starlette.responses import FileResponse
 
 from app.api.auth import router as auth_router
 from app.api.chat import router as chat_router
+from app.api.chat_images import router as chat_images_router
 from app.api.chats import (
     public_router as chats_public_router,
 )
@@ -116,6 +117,10 @@ def create_app() -> FastAPI:
     app.include_router(docs_router, prefix="/api")
     app.include_router(git_sources_router, prefix="/api")
     app.include_router(chat_router, prefix="/api")
+    # Phase 123: the question-image upload/serve pair (POST is
+    # user-gated like the chat turn; GET is public like saved-chat
+    # content — the uuid filename is the credential).
+    app.include_router(chat_images_router, prefix="/api")
     app.include_router(steering_router, prefix="/api")
     app.include_router(sync_router, prefix="/api")
     app.include_router(chats_router, prefix="/api")

app/rag/agent.py

@@ -1393,7 +1393,7 @@ async def run_agent(
     db_factory: Callable[[], Session],
     *,
     system_prompt: str,
-    user_message: str,
+    user_message: str | list[dict[str, Any]],
     seed_docs: Sequence[Document],
     settings: Settings,
     holder: AgentHolder,
@@ -1424,6 +1424,20 @@ async def run_agent(
     unchanged. ``()`` (the default) keeps the pre-phase-74 two-message
     request byte-identical.
 
+    User message (phase 123, TODO L6): *user_message* is the current
+    turn's user content — the plain question string (every text-only
+    turn, byte-identical to pre-phase) OR the multimodal content list
+    ``[{type: "text", …}, {type: "image_url", …}]`` for a question that
+    carried an image. FLOW (pinned): the API layer
+    (``app.api.chat``) builds the content via its ``build_user_content``
+    helper and passes it HERE — ``run_agent`` builds its OWN
+    ``[system, *history, user]`` list from this value (it does NOT
+    receive the already-built ``messages``; the deflected branch is the
+    one that consumes chat.py's list directly), so a single value
+    covers both shapes and the tool rounds / recovery / retries operate
+    on it untouched. Prior turns' images are never replayed (LOCKED A7
+    — *history* is text-only by construction).
+
     Retries (phase 67, owner-locked A2): every model request goes through
     :func:`chat_stream_retried` — a failed round is retried **before** its
     first piece (same messages, ``settings.llm_retries`` restarts, a flat

app/rag/llm.py

@@ -487,11 +487,15 @@ class LLMClient:
 
         Messages are passed to the request body VERBATIM: string-only
         ``{role, content}`` dicts are byte-identical on the wire to the
-        pre-phase-74 requests, and an assistant message may additionally
+        pre-phase-74 requests, an assistant message may additionally
         carry ``reasoning_content`` (the client's prior thinking, phase
         74 — the same wire field the model uses for its OWN reasoning on
-        the response side; the ``openai`` SDK passes message dicts
+        the response side), and a user message's content may be the
-        through untouched, so no transport change).
+        multimodal parts list of a question that carried an image
+        (phase 123 — ``[{type: "text", …}, {type: "image_url", …}]``,
+        built by ``app.api.chat.build_user_content``); the ``openai``
+        SDK passes message dicts through untouched, so no transport
+        change covers all three shapes.
 
         ``stream=True`` against the OpenAI-compatible endpoint, yielding
         typed :class:`StreamPiece` values. Wire convention (verified live

app/rag/summarizer.py

@@ -117,6 +117,18 @@ IMAGE_MIMES: dict[str, str] = {
 IMAGE_FALLBACK_MIME = "application/octet-stream"
 
 
+def image_data_url(data: bytes, mime: str) -> str:
+    """One image's bytes as a data URL for a multimodal message (phase
+    122; factored for phase 123, task 01).
+
+    ``data:<mime>;base64,<ascii>`` — the OpenAI-compatible ``image_url``
+    payload's ``url``. ONE helper, both call sites: :func:`describe_image`
+    (document-image descriptions) and the chat question-image path
+    (``app.api.chat``'s multimodal user message, phase 123).
+    """
+    return f"data:{mime};base64,{base64.b64encode(data).decode('ascii')}"
+
+
 class SummaryLLM(Protocol):
     """The one-shot chat surface the summarizer needs.
 
@@ -223,7 +235,7 @@ async def describe_image(
     the doc is skipped, counted in ``images_failed``, and the sync
     continues (LOCKED A3).
     """
-    data_url = f"data:{mime};base64,{base64.b64encode(data).decode('ascii')}"
+    data_url = image_data_url(data, mime)
     messages: list[dict[str, Any]] = [
         {
             "role": "user",

app/schemas.py

@@ -1,6 +1,7 @@
 """Pydantic request/response schemas (API contract)."""
 from __future__ import annotations
 
+import re
 import uuid
 from datetime import datetime
 from typing import Annotated, Any, Literal
@@ -60,7 +61,8 @@ class HistoryTurn(BaseModel):
 class ChatRequest(BaseModel):
     """``POST /api/chat`` body: the current question plus the optional
     prior turns (phase 74 — the client-provided history, stateless per
-    A10).
+    A10) and, since phase 123, the question's attached image (the
+    stored path — :attr:`image`).
 
     ``history`` is the client's earlier turns, oldest first (the
     ``bor.chat.v1`` record minus the current question); the mapper
@@ -74,6 +76,30 @@ class ChatRequest(BaseModel):
 
     message: str = Field(min_length=1, max_length=4000)
     history: list[HistoryTurn] = Field(default_factory=list, max_length=100)
+    #: Phase 123 (TODO L6, LOCKED A5): the STORED PATH of the question's
+    #: attached image — ``/api/chat-images/<uuid4-hex>.<ext>`` exactly as
+    #: ``POST /api/chat-images`` returns it. NEVER a raw data URL: the
+    #: upload endpoint already did the size/mime enforcement, and
+    #: re-validating a 10 MB base64 string at the schema would be the
+    #: anti-pattern. ``None`` (the default, every text-only question)
+    #: keeps the turn byte-identical to pre-phase-123.
+    image: str | None = Field(default=None, max_length=500)
+
+    @field_validator("image")
+    @classmethod
+    def _image_is_stored_path(cls, v: str | None) -> str | None:
+        """A set ``image`` must be the upload endpoint's stored-path
+        shape — ``/api/chat-images/<uuid4().hex>.<ext>`` (32 hex chars,
+        the six image extensions; the pattern is pinned in the
+        phase-123 design and mirrored by the serve route's filename
+        guard, ``app.api.chat_images``). A data URL, a bare filename, a
+        traversal, a wrong extension, or a mistyped uuid all 422 with
+        ONE fixed detail — no echo of the input."""
+        if v is None:
+            return v
+        if re.fullmatch(r"/api/chat-images/[0-9a-fA-F]{32}\.(png|jpe?g|webp|gif|bmp)", v) is None:
+            raise ValueError("image must be an uploaded chat image path")
+        return v
 
 class LoginRequest(BaseModel):
     """``POST /api/login`` body (phase 16): the single admin's password.
@@ -928,6 +954,36 @@ class ChatMessage(BaseModel):
     # persisted error detail (the phase-48 ``stopped`` precedent).
     failed: bool | None = None
     error: str | None = Field(default=None, max_length=500)
+    # Phase 123 (task 01, LOCKED A5): the question's attached image —
+    # the STORED PATH (``/api/chat-images/<uuid>.<ext>``, from
+    # ``POST /api/chat-images``), on the USER record only: the
+    # attachment belongs to the question, so a brain record never
+    # carries it (the answer may cite the image doc's sources, but the
+    # attachment itself is the user's). The saved/shared shape gains
+    # this one optional key — omitted when ``None`` (the
+    # :meth:`_drop_image_when_absent` serializer below), so a text-only
+    # chat round-trips byte-identically to pre-phase-123 (the
+    # phase-50 contract; the phase-122 ``SourceRef.image_url``
+    # omission precedent). The path is ≤ 500 chars — no phase-83
+    # cap pressure (it is never a data URL, LOCKED A5).
+    image: str | None = Field(default=None, max_length=500)
+
+    @model_serializer(mode="wrap")
+    def _drop_image_when_absent(self, handler: SerializerFunctionWrapHandler) -> Any:
+        """The phase-123 image omission rule: ``image: None`` (every
+        text-only record, and every pre-phase-123 record) serializes
+        WITHOUT the key — ABSENT, never ``null`` — so the stored
+        ``bor.chat.v1`` JSONB and the saved/shared wire shape stay
+        byte-identical to pre-phase for text-only chats (the phase-50
+        round-trip contract). A record WITH an image keeps the path —
+        the user bubble, the refreshed page, and the shared chat all
+        render it from the served route (the image is part of the
+        chat's content, so it rides the same public/credential-
+        is-the-id trust model)."""
+        data = handler(self)
+        if self.image is None:
+            data.pop("image", None)
+        return data
 
 
 class SavedChatCreate(BaseModel):

frontend/assets/app.js

@@ -306,6 +306,14 @@ const sendBtn = document.querySelector("#send-btn");
 const sendLabel = document.querySelector("#send-label");
 const sendStatus = document.querySelector("#send-status");
 const turnLoader = document.querySelector("#turn-loader"); // phase 109 (D16): the persistent in-turn loader — ships hidden; setUiState is its sole visibility owner
+// Phase 123 (task 02, TODO L6): the attach control family — the
+// paperclip button (hidden until the boot /api/config says
+// `images: true`), its hidden file-input backend, the preview strip
+// (hidden until a pick), and the strip's remove button.
+const attachBtn = document.querySelector("#attach-btn");
+const attachFile = document.querySelector("#attach-file");
+const attachPreview = document.querySelector("#attach-preview");
+const attachRemove = document.querySelector("#attach-remove");
 const banner = document.querySelector("#kb-banner");
 const bannerText = document.querySelector("#kb-banner-text");
 const versionEl = document.querySelector("#app-version");
@@ -927,8 +935,17 @@ const USER_AVATAR =
  * scrolls only when the caller passes `scroll = true` — the user submit
  * (reveal my message) and the phase-14 restore landing. The streaming
  * path (thinking / tool / delta) creates bubbles with the default
- * (scroll = false): the page never follows a turn. */
+ * (scroll = false): the page never follows a turn.
-function addMessage(who, html, scroll = false) {
+ *
+ * Phase 123 (task 02, TODO L6): the optional `image` argument —
+ * { src, alt } for a USER bubble carrying the question's attached
+ * image (attachedImage → the live data URL; task 03's restore → the
+ * stored path). The attachment is part of the question, so the img
+ * lands at the TOP of the bubble (above the text) through
+ * attachBubbleImage — ONE renderer for live + restore + shared. A
+ * null image (every text-only message, every brain message) leaves
+ * the bubble byte-identical to pre-phase. */
+function addMessage(who, html, scroll = false, image = null) {
   if (emptyState) emptyState.hidden = true;
   const wrap = document.createElement("div");
   wrap.className = `msg ${who}`;
@@ -937,11 +954,45 @@ function addMessage(who, html, scroll = false) {
     <div class="msg-body">
       <div class="bubble">${html}</div>
     </div>`;
+  if (who === "user" && image) {
+    attachBubbleImage(wrap.querySelector(".bubble"), image.src, image.alt);
+  }
   messagesEl.appendChild(wrap);
   if (scroll) scrollReveal(wrap);
   return wrap;
 }
 
+/* Phase 123 (task 02, TODO L6): the question's image in a user bubble
+ * — the ONE renderer (task 03 reuses it for the restore and the shared
+ * page): the img is built createElement-style (no HTML strings, the
+ * house rule), capped height + full-width safe (a tall portrait must
+ * not blow the chat column — .msg-image in styles.css), lazy-loaded
+ * (the restore's stored paths re-fetch on demand), alt = the
+ * accessible name (the filename live, task 03's restore choice). The
+ * image PREPENDS the text: the attachment is part of the question. */
+function attachBubbleImage(bubble, src, alt) {
+  const img = document.createElement("img");
+  img.className = "msg-image";
+  img.src = src;
+  img.alt = alt || "attached image";
+  img.loading = "lazy";
+  // Phase 123 (task 03, TODO L6): the load failure — the STORED file
+  // was deleted out-of-band (the record keeps its path, the render
+  // degrades): the img is replaced IN PLACE by the small "image
+  // unavailable" line (never a broken-image icon). In practice only
+  // the restore's stored path can 404 (a live data URL is inline); the
+  // shared page carries its own copy of the same degradation (the
+  // per-page duplication house style).
+  img.onerror = () => {
+    const note = document.createElement("span");
+    note.className = "msg-image-unavailable";
+    note.textContent = "image unavailable";
+    img.replaceWith(note);
+  };
+  bubble.prepend(img);
+  return img;
+}
+
 function addTyping() {
   removeTyping(); // idempotent: at most one indicator at a time
   if (emptyState) emptyState.hidden = true;
@@ -1268,6 +1319,26 @@ let leavePartialIndex = -1; // index of this turn's pagehide partial (-1 = none)
 let turnAbort = null; // AbortController of the in-flight turn (null idle)
 let stoppedByUser = false; // the Stop button took this turn (not the guard)
 
+/* Phase 123 (task 02, TODO L6; locked A5): the composer's ATTACHED
+ * image — the { file, name, dataUrl } triple, held until send. The
+ * bytes NEVER touch the chat payload: the send flow uploads the File
+ * to POST /api/chat-images and the record + the request body carry the
+ * returned STORED PATH (A5: never base64). The data URL feeds two
+ * local things only — the preview thumbnail and the LIVE user bubble
+ * (no fetch needed); the restore (task 03) re-renders from the stored
+ * path instead. null = no attachment — the text-only path, byte-
+ * identical to pre-phase (request body, record, bubble). */
+let attachedImage = null;
+let attachUpload = false; // phase 123: one upload at a time (double-fire guard — the upload is the first await in handleSend; a second submit mid-upload is a no-op, the first owns the send)
+
+/* The six extensions the upload endpoint accepts (phase 122's image
+ * set, one list — the server re-validates on the upload; this pre-check
+ * only keeps a bad pick from opening a state change + a wasted
+ * round-trip, and it checks the file NAME's extension: the accept
+ * attribute is advisory, and a drag-pasted or renamed file can carry
+ * any extension the server will 422 anyway). */
+const ATTACHABLE_IMAGE_EXTENSIONS = ["bmp", "gif", "jpeg", "jpg", "png", "webp"];
+
 function stopThinkingClock() {
   if (thinkingClock) {
     clearInterval(thinkingClock);
@@ -1788,7 +1859,22 @@ function renderStoredMessage(m) {
   // the default SCROLL (smooth; "auto" under prefers-reduced-motion)
   // instead of the old forced "auto" — noted per the phase-42 task.
   if (m.who === "user") {
-    addMessage("user", renderMarkdown(m.text), true);
+    const wrap = addMessage("user", renderMarkdown(m.text), true);
+    // Phase 123 (task 03, TODO L6): the restored record may carry the
+    // question's attached image — `m.image`, the STORED PATH (A5:
+    // never base64; a pre-phase / text-only record has no key at all,
+    // so it renders byte-identically — no img). It lands through the
+    // SAME one bubble-image renderer the live send uses
+    // (attachBubbleImage — the live bubble passed the data URL, the
+    // restore passes the stored path; the helper takes any src): the
+    // img at the top of the user bubble, above the text. A load
+    // failure degrades inside the helper (deleted out-of-band file →
+    // the small "image unavailable" line, never a broken icon). A
+    // re-ask (retryLastTurn) re-sends prev.text only (locked A7) —
+    // this bubble's restored attachment is untouched by the redo.
+    if (typeof m.image === "string" && m.image) {
+      attachBubbleImage(wrap.querySelector(".bubble"), m.image, m.text || "attached image");
+    }
     return;
   }
   const wrap = addMessage("brain", renderMarkdown(m.text), true);
@@ -2355,6 +2441,7 @@ function startNewChat() {
   input.value = "";
   autoGrow();
   updateCharCount(); // phase 104: the cleared composer hides the counter again
+  clearAttachedImage(); // phase 123: the attachment is composer draft state — it resets with the conversation
   input.focus();
   sendStatus.textContent = "New chat started — previous conversation cleared.";
 }
@@ -2460,6 +2547,70 @@ function retryLastTurn(wrap) {
   return runTurn(text, { reask: true });
 }
 
+/* Phase 123 (task 02, TODO L6): the send flow's UPLOAD STEP (locked
+ * A8) — the attached File goes to POST /api/chat-images as multipart
+ * (the session cookie rides the browser; the endpoint is user-gated
+ * like the turn it feeds) and the returned STORED path is what the
+ * record + the /api/chat body carry (A5: never base64). ANY failure —
+ * 413 over the cap, 422 a bad extension (a renamed file the client
+ * pre-check missed), 5xx, or a network drop — settles the
+ * phase-114-style OUT-OF-TURN banner with the server's detail and
+ * returns null: the send is BLOCKED (the question is never sent without
+ * the image the user attached — the typed text stays, the attachment
+ * stays for the retry). */
+async function uploadAttachedImage(file) {
+  let res;
+  try {
+    const form = new FormData();
+    form.append("file", file);
+    res = await fetch("/api/chat-images", { method: "POST", body: form });
+  } catch {
+    // Network drop before the server answered — no detail to show.
+    showErrorBanner("Couldn't attach the image — try again.");
+    return null;
+  }
+  let detail = "";
+  let path = null;
+  try {
+    const body = await res.json();
+    if (typeof body?.detail === "string") detail = body.detail;
+    if (typeof body?.path === "string") path = body.path;
+  } catch { /* non-JSON error body — the status line stands in */ }
+  if (!res.ok || !path) {
+    showErrorBanner(
+      detail
+        ? `Couldn't attach the image — ${detail}.`
+        : "Couldn't attach the image — try again."
+    );
+    return null;
+  }
+  return path;
+}
+
+/* Phase 123 (task 02, TODO L6): the preview strip — revealed with the
+ * attached image's data-URL thumbnail + filename (the thumbnail is
+ * decorative, alt="" in the static markup — the filename beside it is
+ * the readable label), and cleared with the attachment (the remove button,
+ * the send, or a New chat). The strip's markup is static (hidden by
+ * default); only the thumbnail's src + the name's textContent move
+ * here (the createElement/textContent house rule — no HTML strings).
+ * Idempotent: a fresh pick re-renders the same strip in place. */
+function showAttachPreview() {
+  if (!attachedImage || !attachPreview) return;
+  attachPreview.querySelector("img").src = attachedImage.dataUrl;
+  attachPreview.querySelector(".attach-preview-name").textContent = attachedImage.name;
+  attachPreview.hidden = false;
+}
+
+/* Phase 123 (task 02, TODO L6): clear the attachment + hide the strip
+ * (idempotent — calling it with nothing attached is a no-op). The
+ * strip must not linger into a turn, and a New chat resets the
+ * composer's draft (the question text + its attachment) together. */
+function clearAttachedImage() {
+  attachedImage = null;
+  if (attachPreview) attachPreview.hidden = true;
+}
+
 async function handleSend(e) {
   e.preventDefault();
   // Phase 48: while a turn is in flight the Send button IS the Stop
@@ -2479,6 +2630,26 @@ async function handleSend(e) {
     showErrorBanner("Questions are limited to 4,000 characters — trim the question and try again.");
     return;
   }
+  // Phase 123 (task 02, TODO L6; locked A8): an attached image uploads
+  // FIRST — BEFORE the input is cleared, so a failed upload BLOCKS the
+  // send and the typed question stays exactly where the user left it
+  // (the question is never sent without the image the user attached;
+  // the banner says what failed, the attachment stays for the retry).
+  // The returned STORED path (never the bytes, A5) then rides runTurn
+  // into the record + the request body.
+  let image = null; // { path, src, alt } | null — null = text-only send
+  if (attachedImage) {
+    if (attachUpload) return; // a second submit mid-upload: the first owns the send (never two uploads, never two turns)
+    attachUpload = true;
+    const path = await uploadAttachedImage(attachedImage.file);
+    attachUpload = false; // the helper never throws (every failure path is a banner + null)
+    if (path === null) return; // A8: the send is blocked — the question stays
+    image = {
+      path, // the record + the /api/chat body (A5: the path, never base64)
+      src: attachedImage.dataUrl, // the live bubble (no fetch); restore uses the path
+      alt: attachedImage.name, // the filename (task 03's restore picks its own alt)
+    };
+  }
   // Phase 49: the user append + persistence save point 1 moved into
   // runTurn with the rest of the turn — the `reask` flag skips them on
   // the redo-in-place retry path (the question is already in the DOM +
@@ -2487,7 +2658,7 @@ async function handleSend(e) {
   autoGrow();
   updateCharCount(); // phase 104: the sent question clears the counter with the input
   clearErrorBanner();
-  await runTurn(text, { reask: false });
+  await runTurn(text, { reask: false, image });
 }
 
 /* Phase 120 (TODO.md L3–4, locked A1): the single funnel for every
@@ -2561,17 +2732,38 @@ function finalizeFailedTurn(detail, { acc, thinking, tools, wrap, leavePartialIn
  * finally settle moved here verbatim, and the turn-local resets (acc,
  * thinkingAcc, sawThinking, sawDone, toolAcc, stoppedByUser, turnAbort)
  * stay turn-scoped exactly as phase 48 left them. */
-async function runTurn(text, { reask = false } = {}) {
+async function runTurn(text, { reask = false, image = null } = {}) {
   if (!reask) {
-    addMessage("user", renderMarkdown(text), true); // reveal my message (owner-kept)
+    // Phase 123 (task 02, TODO L6): the attached image rides the user
+    // bubble (the data URL live — the stored path is the fallback, so
+    // any future caller passing only a path still renders) and the
+    // STORED RECORD (the path, A5: never base64). A null image (every
+    // text-only send, every re-ask — A7: a redo re-sends the text
+    // only) leaves the bubble and the record byte-identical to
+    // pre-phase.
+    addMessage(
+      "user",
+      renderMarkdown(text),
+      true, // reveal my message (owner-kept)
+      image ? { src: image.src || image.path, alt: image.alt } : null
+    );
     // Persistence save point 1: the question is stored the moment it is
-    // sent, so a failed/interrupted turn never loses it.
+    // sent, so a failed/interrupted turn never loses it. The `image`
-    conversation.push({ who: "user", text });
+    // key (the stored path) joins the `bor.chat.v1` record only when an
+    // attachment exists (A5 — the phase-14 shape gains one optional key;
+    // a text-only record is byte-identical to pre-phase).
+    conversation.push(
+      image ? { who: "user", text, image: image.path } : { who: "user", text }
+    );
     saveConversation();
     // Phase 55 (A2): the auto-save rides the save point — an unlinked
     // conversation creates its row here (auto-title, server-side), a
     // linked one refreshes. Fire-and-forget: it never blocks the turn.
     persistConversation();
+    // Phase 123 (task 02): the strip must not linger into the turn —
+    // cleared AFTER the bubble is rendered (the bubble already holds
+    // the image; the record holds the path; a failed turn keeps both).
+    clearAttachedImage();
   }
 
   let wrap = null;
@@ -2632,10 +2824,19 @@ async function runTurn(text, { reask = false } = {}) {
       text: m.text,
       thinking: m.who === "brain" ? m.thinking || undefined : undefined,
     }));
+    // Phase 123 (task 02, TODO L6): the attached image's STORED path
+    // rides the body top-level (A5: the path, never base64; the server
+    // builds the multimodal content from the stored bytes). Added only
+    // when present — a text-only body omits the `image` key entirely
+    // (byte-identical to pre-phase). HISTORY entries stay {who, text,
+    // thinking}: prior turns' images are never replayed (locked A7 —
+    // the image is turn-local to the original send).
+    const payload = { message: text, history };
+    if (image) payload.image = image.path;
     res = await fetch("/api/chat", {
       method: "POST",
       headers: { "Content-Type": "application/json" },
-      body: JSON.stringify({ message: text, history }),
+      body: JSON.stringify(payload),
       signal: turnAbort.signal, // phase 48: the Stop button aborts the fetch
     });
     if (!res.ok || !res.body) {
@@ -3008,6 +3209,48 @@ input.addEventListener("keydown", (e) => {
 });
 composer.addEventListener("submit", handleSend);
 
+/* Phase 123 (task 02, TODO L6): the attach flow. The button (revealed
+ * at boot ONLY when the config flag says images on) opens the hidden
+ * file input; a pick is validated CLIENT-side against the six
+ * extensions (the server re-validates on upload — a bad pick gets the
+ * out-of-turn banner and NO state change: a previous attachment, if
+ * any, survives), then the { file, name, dataUrl } triple lives in
+ * attachedImage until the send flow uploads it. The remove button clears
+ * the state + hides the strip; a fresh pick replaces the triple in
+ * place (the strip re-renders through showAttachPreview). */
+attachBtn?.addEventListener("click", () => attachFile?.click());
+attachRemove?.addEventListener("click", () => {
+  clearAttachedImage();
+  attachBtn?.focus(); // back to the trigger (reachable only while the strip is visible — which means the button is too)
+});
+attachFile?.addEventListener("change", () => {
+  const file = attachFile.files && attachFile.files[0];
+  attachFile.value = ""; // the same file re-picked must fire change again
+  if (!file) return;
+  // The file NAME's extension (lowercased) is the client pre-check —
+  // the accept attribute is advisory (a renamed file can carry any
+  // extension); the upload endpoint is the authority (422).
+  const dot = file.name.lastIndexOf(".");
+  const ext = dot >= 0 ? file.name.slice(dot + 1).toLowerCase() : "";
+  if (!ATTACHABLE_IMAGE_EXTENSIONS.includes(ext)) {
+    showErrorBanner(
+      "Only PNG, JPEG, WebP, GIF, and BMP images can be attached."
+    );
+    return; // no state change — a previous attachment survives
+  }
+  const reader = new FileReader();
+  reader.onload = () => {
+    attachedImage = { file, name: file.name, dataUrl: String(reader.result) };
+    showAttachPreview();
+  };
+  reader.onerror = () => {
+    // The bytes never became readable (the file evicted mid-pick) —
+    // the same copy as an upload failure; no state change.
+    showErrorBanner("Couldn't attach the image — try again.");
+  };
+  reader.readAsDataURL(file);
+});
+
 /* Phase 55 (owner-locked A2, 2026-08-31): the phase-50 Save binding is
  * GONE with the pill — there is no Save control; persistConversation()
  * auto-saves headless at the save points (fire-and-forget, quiet on
@@ -3086,8 +3329,17 @@ window.addEventListener("pagehide", () => {
   // proven), so a restored conversation of a configured admin gets the
   // "Save as doc" button exactly once: no flash, no re-render, no
   // second fetch (the brand fetch IS the config fetch).
-  await (window.BOR_CONFIG_PROMISE ?? Promise.resolve());
+  const bootConfig = await (window.BOR_CONFIG_PROMISE ?? Promise.resolve());
   docsRepoConfigured = window.BOR_DOCS_REPO_CONFIGURED === true;
+  // Phase 123 (task 02, TODO L6): the attach control reveals ONLY when
+  // the SAME settled config says images: true (the brand boot's ONE
+  // /api/config request — no second round-trip). Off (the default) or
+  // an unanswered fetch → the button stays hidden for good: the
+  // flag-off DOM is byte-identical to pre-phase (A5's default-off
+  // contract), and a degraded boot degrades quietly (the loadHealth
+  // house style — the page never breaks, the affordance is simply
+  // absent; the API contract still enforces the toggle server-side).
+  if (attachBtn) attachBtn.hidden = bootConfig?.images !== true;
   applyAuthState(); // chat page: the auth pair (idempotent with header.js)
   // Phase 55 (task 03): no Share-reveal step — the pill is static,
   // always-visible markup (visible to every visitor, phase 51 contract).

frontend/assets/shared.js

@@ -318,9 +318,42 @@ function addStoppedNote(wrap) {
   meta.appendChild(note);
 }
 
+/* The question's attached image (phase 123, task 03, TODO L6) — the
+ * local copy of the chat page's attachBubbleImage (the per-page
+ * duplication house style: this file keeps its own small copies of
+ * the chat page's message-fragment builders). The SAME .msg-image
+ * treatment the chat page uses — styles.css is shared by both pages,
+ * so the rule needs no second copy: the img at the TOP of the user
+ * bubble (the attachment is part of the question), lazy, alt = the
+ * record's text or the fallback. The load failure degrades IDENTICALLY
+ * to the chat page: the img is replaced by the small "image
+ * unavailable" line (the stored file was deleted out-of-band — the
+ * record keeps its path, the render degrades; never a broken icon).
+ * The serve route is public (the token is the shared chat's
+ * credential, like saved-chat content), so the img loads for guests
+ * exactly as it does for the owner. */
+function addBubbleImage(wrap, src, alt) {
+  const bubble = wrap?.querySelector?.(".bubble");
+  if (!bubble) return;
+  const img = document.createElement("img");
+  img.className = "msg-image";
+  img.src = src;
+  img.alt = alt || "attached image";
+  img.loading = "lazy";
+  img.onerror = () => {
+    const note = document.createElement("span");
+    note.className = "msg-image-unavailable";
+    note.textContent = "image unavailable";
+    img.replaceWith(note);
+  };
+  bubble.prepend(img);
+}
+
 /* One stored record through the SAME .msg structure the chat page
  * uses (pixel-parity with the chat page's restore path): user → the
- * .msg.user bubble; brain → the .msg.brain bubble with the optional
+ * .msg.user bubble (with the question's attached image when the
+ * record carries the stored path — phase 123, task 03); brain → the
+ * .msg.brain bubble with the optional
  * thinking block (restored COLLAPSED — phase 17), the tool lines,
  * the deflection treatment + the plain-text "Maybe try" chips, the
  * plain-text source chips, and the stopped note. NO interactive
@@ -331,7 +364,16 @@ function addStoppedNote(wrap) {
  * unchanged. */
 function renderSharedMessage(m) {
   if (m.who === "user") {
-    addSharedMessage("user", renderMarkdown(m.text));
+    const wrap = addSharedMessage("user", renderMarkdown(m.text));
+    // Phase 123 (task 03, TODO L6): the question's attached image —
+    // the record's `m.image` carries the STORED PATH (A5: never
+    // base64; a pre-phase record has no key at all, so it renders
+    // byte-identically — no img). The public image route makes the
+    // shared view faithful: the SAME bubble treatment, alt, and
+    // load-failure degradation as the chat page's restore.
+    if (typeof m.image === "string" && m.image) {
+      addBubbleImage(wrap, m.image, m.text || "attached image");
+    }
     return;
   }
   const wrap = addSharedMessage("brain", renderMarkdown(m.text));

frontend/assets/styles.css

@@ -551,6 +551,42 @@ body::before {
 }
 .msg.user .bubble code { background: color-mix(in srgb, var(--bg) 16%, transparent); }
 
+/* Phase 123 (task 02, TODO L6): the question's IMAGE in the user
+   bubble — the attachment is PART of the question, so it sits at the
+   TOP of the bubble (above the text). Capped height (a tall portrait
+   must not blow the chat column) + full-width safe; the theme's
+   bordered-image treatment (the .source-image-img language) — the
+   border gives the bytes a boundary against the brand bubble fill. */
+.msg-image {
+  display: block;
+  width: auto;
+  height: auto;
+  max-width: 100%;
+  max-height: 240px;
+  object-fit: contain;
+  border: 1px solid var(--line);
+  border-radius: var(--radius-sm);
+  margin-bottom: 0.45rem;
+}
+
+/* Phase 123 (task 03, TODO L6): the question's image is UNAVAILABLE —
+   the stored file was deleted out-of-band (the record keeps its
+   path, the render degrades): the small muted line takes the img's
+   place at the top of the user bubble on BOTH pages (the chat
+   restore and the shared view render the same record shape through
+   the same .msg/.bubble structure, and share this stylesheet). It
+   inherits the bubble's text color — the user bubble's text already
+   passes 4.5:1 (PLAN §7.2), so the note does too; the smaller size +
+   italic make it read as a note, never a broken-image icon. The
+   margin-bottom mirrors .msg-image's, so the text below keeps its
+   spacing either way. */
+.msg-image-unavailable {
+  display: block;
+  margin-bottom: 0.45rem;
+  font-size: 0.75rem;
+  font-style: italic;
+}
+
 .msg.brain .bubble { border-bottom-left-radius: 4px; }
 .msg.brain.is-deflected .bubble {
   background: var(--accent-bg);
@@ -1581,6 +1617,62 @@ details.thinking .thinking-text ul { margin: 0 0 0.5rem; }
    color, never color alone (B3). */
 .char-count { margin: 0; text-align: right; font-size: 0.75rem; line-height: 1.2; color: var(--ink-soft); }
 .char-count.is-max { color: var(--err-ink); }
+/* Phase 123 (task 02, TODO L6): the ATTACH PREVIEW STRIP — the
+   selected image ABOVE the input row (thumbnail ≤48px + the filename
+   + the remove button): a surface card in the .chat-bottom stack, between
+   the char-count line and the composer. The name is ellipsized
+   (AA-safe --ink on --surface = 13.8:1) — a long filename never widens
+   the strip; the thumbnail is a fixed 48px cover box (the preview
+   crops, the bubble shows the whole image); the remove button keeps the
+   44px touch
+   target (PLAN §7.1) with a destructive hover (--err-ink on --err-bg =
+   9.3:1 — text + color, never color alone, B3). Hidden by default
+   (the global [hidden] rule) — revealed only while a file is attached,
+   cleared with the send so the strip never lingers into a turn. */
+.attach-preview {
+  display: flex;
+  align-items: center;
+  gap: 0.5rem;
+  margin: 0 0 0.45rem;
+  padding: 0.35rem 0.5rem;
+  background: var(--surface);
+  border: 1px solid var(--line);
+  border-radius: var(--radius-sm);
+}
+.attach-preview-img {
+  flex: none;
+  width: 48px;
+  height: 48px;
+  object-fit: cover;
+  border: 1px solid var(--line);
+  border-radius: 4px;
+  background: var(--bg);
+}
+.attach-preview-name {
+  flex: 1;
+  min-width: 0;
+  overflow: hidden;
+  text-overflow: ellipsis;
+  white-space: nowrap;
+  font-size: 0.85rem;
+  color: var(--ink);
+}
+.attach-preview-remove {
+  display: inline-flex;
+  align-items: center;
+  justify-content: center;
+  flex: none;
+  width: 44px;
+  min-height: 44px;
+  border: 0;
+  border-radius: var(--radius-sm);
+  background: transparent;
+  color: var(--ink-soft);
+  cursor: pointer;
+  padding: 0;
+}
+.attach-preview-remove svg { width: 18px; height: 18px; }
+.attach-preview-remove:hover { background: var(--err-bg); color: var(--err-ink); }
 .composer {
   display: flex;
   align-items: flex-end;
@@ -1605,6 +1697,31 @@ details.thinking .thinking-text ul { margin: 0 0 0.5rem; }
   background: transparent;
 }
 .composer textarea::placeholder { color: var(--ink-soft); }
+/* Phase 123 (task 02, TODO L6): the composer's ATTACH CONTROL — the
+   paperclip glyph button LEFT of the input. Hidden in the markup until
+   app.js reveals it from the config's images flag (the global [hidden]
+   rule keeps it out of the flag-off DOM — A5's default-off contract).
+   A neutral cut of the .send-btn family: the same 44px hit target +
+   radius + the global :focus-visible ring (PLAN §7.2); surface fill
+   with a muted hover step (the icon: --ink-soft on --surface = 5.1:1,
+   hover --brand-ink on --brand-soft = 12.4:1 — both past the 3:1
+   non-text floor). */
+.attach-btn {
+  display: inline-flex;
+  align-items: center;
+  justify-content: center;
+  flex: none;
+  width: 44px;
+  min-height: 44px;
+  border: 1px solid var(--line);
+  border-radius: var(--radius-sm);
+  background: var(--surface);
+  color: var(--ink-soft);
+  cursor: pointer;
+  padding: 0;
+}
+.attach-btn svg { width: 20px; height: 20px; }
+.attach-btn:hover { background: var(--brand-soft); border-color: var(--brand-soft); color: var(--brand-ink); }
 .send-btn {
   display: inline-flex;
   align-items: center;

frontend/index.html

@@ -267,6 +267,24 @@
              (role=alert). -->
         <p class="char-count" id="char-count" hidden></p>
 
+          <!-- Phase 123 (task 02, TODO L6): the attach PREVIEW STRIP —
+               the selected image (thumbnail ≤48px + the filename + a
+               remove X) ABOVE the input row: the attachment is part of
+               the question being typed. `hidden` by default — app.js
+               reveals it only while a file is attached (attachedImage)
+               and clears it with the send (the strip must not linger
+               into the turn). With no pick — and with the images flag
+               off — it is never visible (A5's default-off contract).
+               The thumbnail is decorative (alt="" — the filename is
+               the visible, readable label beside it). -->
+          <div class="attach-preview" id="attach-preview" hidden>
+            <img class="attach-preview-img" alt="">
+            <span class="attach-preview-name"></span>
+            <button type="button" class="attach-preview-remove" id="attach-remove" aria-label="Remove the attached image">
+              <svg aria-hidden="true" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="1.7" stroke-linecap="round"><path d="M6 6l12 12M18 6L6 18"/></svg>
+            </button>
+          </div>
+
           <!-- Composer (phase 48, 2026-08-29, TODO.md L3): one button, two
                roles — #send-btn reads "Send" when idle and morphs into the
                enabled "Stop" control (.is-stop, rose treatment) while a turn
@@ -284,6 +302,24 @@
                `!text` guard in app.js is the real empty-input check (same
                precedent as the tuning form's noValidate). -->
         <form class="composer" id="composer" novalidate>
+          <!-- Phase 123 (task 02, TODO L6): the attach control — the
+               paperclip glyph button LEFT of the input (the icon style
+               of the other composer glyphs; aria-label is its
+               accessible name, the SVG is decorative). HIDDEN BY
+               DEFAULT — app.js reveals it only when the boot
+               /api/config says `images: true` (the brand boot's ONE
+               config request — no second round-trip); flag off (the
+               default) keeps the button hidden for good, so the
+               flag-off DOM is byte-identical to pre-phase (A5's
+               default-off contract). The hidden #attach-file input is
+               its backend (a programmatic .click() — the native
+               picker); accept mirrors the server's six-extension gate
+               (the client re-checks the name's extension before any
+               state change; the upload endpoint is the authority). -->
+          <button type="button" class="attach-btn" id="attach-btn" hidden aria-label="Attach an image">
+            <svg aria-hidden="true" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="1.7" stroke-linecap="round" stroke-linejoin="round"><path d="M21.44 11.05l-9.19 9.19a6 6 0 0 1-8.49-8.49l9.19-9.19a4 4 0 0 1 5.66 5.66l-9.2 9.19a2 2 0 0 1-2.83-2.83l8.49-8.48"/></svg>
+          </button>
+          <input type="file" id="attach-file" accept="image/png,image/jpeg,image/webp,image/gif,image/bmp" hidden>
           <label class="visually-hidden" for="message-input">Ask Brain of Reese a question</label>
           <!-- maxlength=4000 mirrors ChatRequest.message max_length=4000
                (app/schemas.py) — the server 422s beyond; the #char-count

tests/e2e/mock_llm.py

@@ -1083,6 +1083,16 @@ _HTTPS_PER_DEAD_ATTEMPT = 3
 #: re-drives the failure sequence from zero.
 _fail_posts: dict[str, int] = {}
 
+#: Phase 123 (task 04 — question images): a small ring buffer of the
+#: recent ``/v1/chat/completions`` request bodies, exposed on the
+#: ``/v1/e2e/captured`` pair below. Purely OBSERVATIONAL (the buffer
+#: never influences an answer — determinism is untouched): it lets a
+#: story suite assert on the EXACT request the app built — e.g. that a
+#: question-image turn delivered the multimodal user content list
+#: (text part + ``image_url`` data URL) to the model.
+_CAPTURED: list[dict[str, Any]] = []
+_CAPTURE_MAX = 100
+
 
 def _llm_500(why: str) -> JSONResponse:
     """A dead-proxy 500 with a JSON error body (phase 67 injection)."""
@@ -2416,6 +2426,23 @@ def compose_thinking_paragraphs(body: dict[str, Any]) -> str:
     return "\n".join(out)
 
 
+@app.get("/v1/e2e/captured")
+def e2e_captured() -> list[dict[str, Any]]:
+    """Phase 123 (task 04): the recent chat-completions request bodies
+    (oldest first, capped at ``_CAPTURED_MAX``) — the mock's capture
+    for request-shape assertions (see ``_CAPTURED``)."""
+    return _CAPTURED
+
+
+@app.post("/v1/e2e/captured/reset")
+def e2e_captured_reset() -> dict[str, int]:
+    """Phase 123 (task 04): clear the capture so a suite can assert on
+    exactly the requests of the turn it is about to drive (e.g. the
+    toggle-off rejection proves ZERO chat calls — an empty capture)."""
+    _CAPTURED.clear()
+    return {"cleared": True}
+
+
 @app.post("/__shutdown__")
 def shutdown() -> dict[str, Any]:
     """Test hook (loading-feedback story): terminate this mock process to
@@ -2619,6 +2646,12 @@ def _tool_call_stream(name: str, arguments: dict[str, Any], call_id: str) -> Any
 
 @app.post("/v1/chat/completions")
 def chat_completions(body: dict[str, Any]) -> Any:
+    # Phase 123 (task 04): the OBSERVATIONAL capture (the ring buffer —
+    # recorded before any flow decision, so a 500-injected request is
+    # captured too; the buffer never touches the answer path).
+    _CAPTURED.append(body)
+    if len(_CAPTURED) > _CAPTURE_MAX:
+        del _CAPTURED[: len(_CAPTURED) - _CAPTURE_MAX]
     user_lower = _user(body).lower()
     # Phase 37 (agent document tools): the deterministic marker flow.
     # The app's chat path is the only streaming consumer of this mock, so

tests/e2e/test_chat_image_questions.py

@@ -0,0 +1,626 @@
+"""Phase 123 E2E (Playwright): chat image questions — attach an image to a
+question (TODO L6).
+
+Run in isolation (DB must be up: ``podman compose up -d db``):
+
+    uv run pytest tests/e2e/test_chat_image_questions.py -v --no-cov
+
+The suite's app instance runs with ``BOR_IMAGES=true`` (module env
+override — the conftest per-suite-app pattern, leak guards included;
+the question-image store is a suite-private scratch dir so the app
+under test never writes into the owner's real ``~/bor-sources``), and
+a SECOND module app runs with ``BOR_IMAGES`` forced ``false`` (the
+default contract — both apps pin the toggle EXPLICITLY, so an
+operator's local ``.env`` cannot leak it in either direction).
+
+The KB is deliberately NOT seeded (each test truncates it): the
+question-image turn is a DETERMINISTIC deflection (no chunks → LOW
+→ the mock's honest "I haven't done anything like that" answer) —
+the deflected branch is a construction site for the multimodal user
+message (pinned by ``app/api/chat.py``'s docstring), and the answer
+the mock streams is independent of the image part (the mock's
+``_content_text`` maps a part list to its text parts).
+
+* attach a fixture PNG in the composer → the preview strip shows
+  (thumbnail ≤48px + the filename) → remove → the strip clears and
+  the file state is gone (a fresh pick re-renders in place);
+* re-attach → send → exactly ONE upload, the user bubble shows the
+  image (the live data URL, alt = the filename), the preview strip
+  must not linger into the turn, the mock's (text-only) answer
+  streams, and — via the mock's capture (``/v1/e2e/captured``) —
+  the model RECEIVED the multimodal user content list (the text
+  part == the question + the ``image_url`` data URL that decodes to
+  the uploaded bytes);
+* the saved record carries the stored PATH (A5: never base64 —
+  nothing base64 crosses the localStorage boundary);
+* ``page.reload()`` → the user bubble restores WITH its image from
+  the stored path (the image route's request count confirms a PATH
+  fetch, not an inline data URL);
+* share the chat → a fresh anonymous context opening the shared link
+  sees the user's image on the shared page (the serve route is
+  public — the shared view is faithful);
+* default-off negative (the flag-off app): ``#attach-btn`` stays
+  hidden for good (the default-off contract) and a direct
+  ``POST /api/chat`` with an ``image`` settles the hinted error
+  frame with ZERO model calls (the capture stays empty).
+"""
+from __future__ import annotations
+
+import base64
+import json
+import os
+import re
+import subprocess
+import sys
+import time
+from collections.abc import Iterator
+from pathlib import Path
+from typing import Any
+
+import httpx
+import pytest
+from playwright.sync_api import Page, expect
+from sqlalchemy import text
+
+from app.config import Settings
+from app.db import SessionLocal
+from e2e.auth_helpers import login
+from e2e.conftest import ADMIN_PASSWORD, SESSION_SECRET, USE_REAL_LLM, _wait_http
+
+REPO = Path(__file__).resolve().parents[2]
+
+#: A real 1×1 transparent PNG (the unit/integration suites' fixture —
+#: the pipeline is content-agnostic; the well-formed bytes keep the
+#: upload + serve + render + capture pins honest).
+PNG_1X1 = base64.b64decode(
+    "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJ"
+    "AAAAC0lEQVR4nGP4DwQACfsD/fteaysAAAAASUVORK5CYII="
+)
+PNG_NAME = "diagram.png"
+
+QUESTION = "What is in this screenshot? (chat-images)"
+TEXT_ONLY_QUESTION = "How is my Kubernetes cluster set up? (chat-images text-only)"
+STORAGE_KEY = "bor.chat.v1"
+DEFLECT_PHRASE = r"haven't done anything like that"
+IMAGE_PATH_RE = re.compile(r"^/api/chat-images/[0-9a-f]{32}\.png$")
+SHARE_URL_RE = re.compile(r"^/shared/[0-9a-f-]{36}$")
+TURN_TIMEOUT_MS = 30_000
+
+
+# ---------------------------------------------------------------------------
+# Module apps: images ON (the story) and images forced OFF (the default
+# contract). Each owns its port + its scratch question-image dir.
+# ---------------------------------------------------------------------------
+
+
+def _app_env(mock_llm: int, app_port: int, *, images: bool, scratch: Path) -> dict[str, str]:
+    """The conftest app env (leak guards included) with the phase-123
+    knobs: ``BOR_IMAGES`` pinned EXPLICITLY (true for the story app,
+    false for the default app — process env ranks above an operator's
+    local gitignored ``.env``, so the contract under test cannot leak
+    in either direction) and the question-image store in the suite's
+    scratch dir (the app under test must not write into the owner's
+    real ``~/bor-sources``)."""
+    env = dict(os.environ)
+    env.pop("DEBUGPY", None)
+    env["BOR_ENVIRONMENT"] = "e2e"
+    env["BOR_STATIC_DIR"] = str(REPO / "frontend")
+    env["BOR_LLM_BASE_URL"] = (
+        "https://aipi.reeseapps.com/v1"
+        if USE_REAL_LLM
+        else f"http://127.0.0.1:{mock_llm}/v1"
+    )
+    # Mock-calibrated gate (conftest pattern) — with an UNSEEDED KB
+    # (this suite's determinism) every turn is a deflection anyway;
+    # the pins keep the gate's quadrant stable if the dev KB leaks in.
+    env["BOR_RELEVANCE_THRESHOLD"] = "0.30"
+    env["BOR_LEXICAL_SUPPORT_FLOOR"] = "0.15"
+    env["BOR_SOURCE_USEFULNESS_FLOOR"] = "0.15"
+    # Phase 67: instant retry waits + the code-default budget.
+    env["BOR_LLM_RETRY_DELAY"] = "0"
+    env["BOR_LLM_RETRIES"] = str(Settings.model_fields["llm_retries"].default)
+    env.setdefault(
+        "BOR_DATABASE_URL",
+        "postgresql+psycopg://reese:reese@localhost:5432/brain_of_reese",
+    )
+    env["BOR_ADMIN_PASSWORD"] = ADMIN_PASSWORD
+    env["BOR_SESSION_SECRET"] = SESSION_SECRET
+    # Leak guards (conftest pattern).
+    env["BOR_DOCS_REPO"] = ""
+    env["BOR_SUGGESTIONS"] = json.dumps(Settings.model_fields["suggestions"].default)
+    env["BOR_INPUT_PLACEHOLDER"] = Settings.model_fields["input_placeholder"].default
+    env["BOR_FOOTER_TEXT"] = Settings.model_fields["footer_text"].default
+    # Phase 123: the toggle under test + the suite-private image store.
+    env["BOR_IMAGES"] = "true" if images else "false"
+    env["BOR_CHAT_IMAGE_DIR"] = str(scratch / "chat-images")
+    return env
+
+
+@pytest.fixture(scope="module")
+def app_server(mock_llm: int, tmp_path_factory: pytest.TempPathFactory) -> Iterator[str]:
+    """The story app — ``BOR_IMAGES=true`` (the module env override;
+    the conftest session app is never started in this isolated run,
+    so no port clash)."""
+    scratch = tmp_path_factory.mktemp("bor_chat_image_on")
+    port = int(os.environ.get("E2E_APP_PORT_CHAT_IMAGES", "8160"))
+    proc = subprocess.Popen(
+        [sys.executable, "-m", "uvicorn", "app.main:app",
+         "--host", "127.0.0.1", "--port", str(port), "--log-level", "warning"],
+        cwd=REPO,
+        env=_app_env(mock_llm, port, images=True, scratch=scratch),
+    )
+    try:
+        _wait_http(f"http://127.0.0.1:{port}/api/health")
+        yield f"http://127.0.0.1:{port}"
+    finally:
+        proc.terminate()
+        try:
+            proc.wait(timeout=10)
+        except subprocess.TimeoutExpired:
+            proc.kill()
+
+
+@pytest.fixture(scope="module")
+def app_url(app_server: str) -> str:
+    return app_server
+
+
+@pytest.fixture(scope="module")
+def default_app_server(
+    mock_llm: int, tmp_path_factory: pytest.TempPathFactory
+) -> Iterator[str]:
+    """The default-contract app — ``BOR_IMAGES=false`` (only the
+    negative test starts it)."""
+    scratch = tmp_path_factory.mktemp("bor_chat_image_off")
+    port = int(os.environ.get("E2E_APP_PORT_CHAT_IMAGES_OFF", "8161"))
+    proc = subprocess.Popen(
+        [sys.executable, "-m", "uvicorn", "app.main:app",
+         "--host", "127.0.0.1", "--port", str(port), "--log-level", "warning"],
+        cwd=REPO,
+        env=_app_env(mock_llm, port, images=False, scratch=scratch),
+    )
+    try:
+        _wait_http(f"http://127.0.0.1:{port}/api/health")
+        yield f"http://127.0.0.1:{port}"
+    finally:
+        proc.terminate()
+        try:
+            proc.wait(timeout=10)
+        except subprocess.TimeoutExpired:
+            proc.kill()
+
+
+@pytest.fixture(scope="module")
+def default_app_url(default_app_server: str) -> str:
+    return default_app_server
+
+
+def _reset_db(mock_port: int, seed: bool) -> None:
+    """Truncate the KB (and the turn log) so every turn in this suite
+    is a deterministic deflection. ``seed`` is always False here — a
+    question image is a separate concern from document ingestion (it
+    is NEVER indexed as a document), so the suite never imports."""
+    with SessionLocal() as db:
+        db.execute(text("TRUNCATE chunks, documents, query_log, steering_notes"))
+        db.commit()
+    assert seed is False
+
+
+# ---------------------------------------------------------------------------
+# Browser helpers (the composer's attach flow + the turn's settle)
+# ---------------------------------------------------------------------------
+
+
+def _png_file(tmp_path: Path) -> Path:
+    png = tmp_path / PNG_NAME
+    png.write_bytes(PNG_1X1)
+    return png
+
+
+def _attach(page: Page, png: Path) -> None:
+    """One file pick in the composer's HIDDEN file input (the
+    paperclip button's backend — the native picker is replaced by
+    ``set_input_files``, the E2E's standard input simulation): the
+    preview strip must reveal with the data-URL thumbnail + name."""
+    page.set_input_files("#attach-file", str(png))
+    strip = page.locator("#attach-preview")
+    expect(strip).to_be_visible(timeout=TURN_TIMEOUT_MS)
+    expect(page.locator("#attach-preview .attach-preview-name")).to_have_text(PNG_NAME)
+    thumb = page.locator("#attach-preview img")
+    src = thumb.get_attribute("src") or ""
+    assert src.startswith("data:image/png;base64,"), "the thumbnail is the live data URL"
+
+
+def _wait_deflected_turn(page: Page) -> None:
+    """Wait until the (unseeded-KB) turn has fully settled — the
+    deflected answer streamed and the Send button is back (the
+    ``done`` frame restored it)."""
+    bubble = page.locator(".msg.brain.is-deflected .bubble").first
+    bubble.wait_for(state="visible", timeout=TURN_TIMEOUT_MS)
+    expect(bubble).to_contain_text(
+        re.compile(DEFLECT_PHRASE, re.IGNORECASE), timeout=TURN_TIMEOUT_MS
+    )
+    expect(page.locator("#send-btn")).to_be_enabled()
+    expect(page.locator("#send-label")).to_have_text("Send")
+
+
+def _stored(page: Page) -> dict[str, Any] | None:
+    raw = page.evaluate(f"() => localStorage.getItem('{STORAGE_KEY}')")
+    return json.loads(raw) if raw else None
+
+
+def _admin_cookies(page: Page) -> dict[str, str]:
+    return {
+        c["name"]: c["value"]
+        for c in page.context.cookies()
+        if "name" in c and "value" in c
+    }
+
+
+def _chats(app_url: str, cookies: dict[str, str]) -> list[dict[str, Any]]:
+    r = httpx.get(f"{app_url}/api/chats", timeout=10, cookies=cookies)
+    assert r.status_code == 200
+    return r.json()["chats"]
+
+
+def _find_row(rows: list[dict[str, Any]], title: str) -> dict[str, Any] | None:
+    return next((c for c in rows if c["title"] == title), None)
+
+
+def _auto_title(question: str) -> str:
+    """The phase-50 auto-title convention: the first question,
+    whitespace-collapsed, capped at 120 chars."""
+    return " ".join(question.split())[:120]
+
+
+def _wait_saved_row(
+    app_url: str,
+    cookies: dict[str, str],
+    title: str,
+    messages: int = 2,
+) -> dict[str, Any]:
+    """Wait for the auto-saved row (phase 55: auto-saves are SILENT —
+    A2 — so there is no status line to wait on)."""
+    deadline = time.monotonic() + 15
+    last: dict[str, Any] | None = None
+    while time.monotonic() < deadline:
+        last = _find_row(_chats(app_url, cookies), title)
+        if last is not None and last["message_count"] >= messages:
+            return last
+        time.sleep(0.2)
+    raise AssertionError(f"no auto-saved row for {title!r} (last: {last!r})")
+
+
+def _delete_row(app_url: str, cookies: dict[str, str], chat_id: str) -> None:
+    """Best-effort row cleanup (a 404 — already deleted — is fine)."""
+    httpx.delete(f"{app_url}/api/chats/{chat_id}", timeout=10, cookies=cookies)
+
+
+def _send_with_attachment(page: Page, png: Path) -> tuple[str, list[str]]:
+    """Attach → type → send → wait for the deflected settle. Returns
+    (the record's stored image PATH, the upload request URLs)."""
+    uploads: list[str] = []
+
+    def _on_request(req: Any) -> None:
+        if req.method == "POST" and req.url.endswith("/api/chat-images"):
+            uploads.append(req.url)
+
+    page.on("request", _on_request)
+    _attach(page, png)
+    page.fill("#message-input", QUESTION)
+    page.click("#send-btn")
+    img = page.locator(".msg.user .msg-image").first
+    expect(img).to_be_visible(timeout=TURN_TIMEOUT_MS)
+    _wait_deflected_turn(page)
+    stored = _stored(page)
+    assert stored is not None, "the conversation must be persisted (save point 1)"
+    path = stored["messages"][0]["image"]
+    assert IMAGE_PATH_RE.fullmatch(path), f"the record must carry the stored PATH: {path!r}"
+    return path, uploads
+
+
+# ---------------------------------------------------------------------------
+# The mock's capture (phase 123, task 04 — the request the SERVER built)
+# ---------------------------------------------------------------------------
+
+
+def _mock_base(mock_llm: int) -> str:
+    return f"http://127.0.0.1:{mock_llm}"
+
+
+def _reset_capture(mock_llm: int) -> None:
+    r = httpx.post(f"{_mock_base(mock_llm)}/v1/e2e/captured/reset", timeout=10)
+    assert r.status_code == 200
+
+
+def _captured(mock_llm: int) -> list[dict[str, Any]]:
+    r = httpx.get(f"{_mock_base(mock_llm)}/v1/e2e/captured", timeout=10)
+    assert r.status_code == 200
+    return r.json()
+
+
+# ---------------------------------------------------------------------------
+# 1. Attach → preview → remove (the composer's draft state)
+# ---------------------------------------------------------------------------
+
+
+def test_attach_preview_shows_and_remove_clears(
+    page: Page, app_url: str, mock_llm: int, db_ready: None, tmp_path: Path
+) -> None:
+    _reset_db(mock_llm, seed=False)
+    page.set_default_timeout(30_000)
+    login(page, app_url, next="/")
+
+    # Flag on (the story app): the paperclip is revealed at boot, with
+    # its accessible name (the SVG is decorative).
+    btn = page.locator("#attach-btn")
+    expect(btn).to_be_visible()
+    expect(btn).to_have_attribute("aria-label", "Attach an image")
+
+    png = _png_file(tmp_path)
+    _attach(page, png)
+
+    # The strip: the data-URL thumbnail + the filename (the readable
+    # label) + the remove ✕ (its accessible name).
+    expect(page.locator("#attach-preview img")).to_be_visible()
+    remove = page.locator("#attach-remove")
+    expect(remove).to_be_visible()
+    expect(remove).to_have_attribute("aria-label", "Remove the attached image")
+
+    # Remove: the strip clears and the file state is GONE — a fresh
+    # pick re-renders the strip in place (the state was truly reset,
+    # not merely hidden under a stale one).
+    page.click("#attach-remove")
+    expect(page.locator("#attach-preview")).to_be_hidden()
+    _attach(page, png)
+    expect(page.locator("#attach-preview")).to_be_visible()
+    expect(page.locator("#attach-preview .attach-preview-name")).to_have_text(PNG_NAME)
+
+
+# ---------------------------------------------------------------------------
+# 2. Send with an attachment: one upload, the image in the bubble, the
+#    multimodal request at the mock, the PATH (never base64) in storage
+# ---------------------------------------------------------------------------
+
+
+def test_send_with_attached_image_delivers_the_multimodal_request(
+    page: Page, app_url: str, mock_llm: int, db_ready: None, tmp_path: Path
+) -> None:
+    _reset_db(mock_llm, seed=False)
+    page.set_default_timeout(30_000)
+    login(page, app_url, next="/")
+    png = _png_file(tmp_path)
+
+    _reset_capture(mock_llm)  # exactly the requests of THIS turn
+    path, uploads = _send_with_attachment(page, png)
+
+    # A8's ordering at the wire level: EXACTLY one upload (the double-
+    # fire guard never let a second through) and it preceded the turn.
+    assert len(uploads) == 1
+
+    # The live user bubble: the data URL (no fetch), alt = the
+    # filename; the preview strip must not linger into the turn.
+    img = page.locator(".msg.user .msg-image").first
+    src = img.get_attribute("src") or ""
+    assert src.startswith("data:image/png;base64,"), "the live bubble uses the data URL"
+    assert base64.b64decode(src.split(",", 1)[1]) == PNG_1X1
+    assert img.get_attribute("alt") == PNG_NAME
+    expect(page.locator("#attach-preview")).to_be_hidden()
+
+    # The mock (text-only) answer streamed normally (the mock ignores
+    # the image part) — and the REQUEST it received is the multimodal
+    # user content list: text part == the question + the image_url
+    # data URL that decodes to the uploaded bytes (the server built
+    # it from the stored file + the phase-122 mime map).
+    captured = _captured(mock_llm)
+    assert len(captured) == 1, "the deflected turn is exactly one model request"
+    user = captured[0]["messages"][-1]
+    assert user["role"] == "user"
+    assert user["content"] == [
+        {"type": "text", "text": QUESTION},
+        {
+            "type": "image_url",
+            "image_url": {
+                "url": f"data:image/png;base64,{base64.b64encode(PNG_1X1).decode('ascii')}"
+            },
+        },
+    ]
+
+    # A5 at the storage boundary: the record carries the PATH, and
+    # NOTHING base64 crossed into the localStorage payload.
+    stored = _stored(page)
+    assert stored is not None
+    assert stored["messages"][0]["image"] == path
+    assert "base64" not in json.dumps(stored)
+
+    # Cleanup: drop the auto-saved row (the dev DB is shared).
+    cookies = _admin_cookies(page)
+    row = _wait_saved_row(app_url, cookies, _auto_title(QUESTION))
+    _delete_row(app_url, cookies, row["id"])
+
+
+# ---------------------------------------------------------------------------
+# 3. Reload: the user bubble restores WITH its image (from the stored
+#    path — the image route's request count confirms the path fetch)
+# ---------------------------------------------------------------------------
+
+
+def test_reload_restores_the_image_from_the_stored_path(
+    page: Page, app_url: str, mock_llm: int, db_ready: None, tmp_path: Path
+) -> None:
+    _reset_db(mock_llm, seed=False)
+    page.set_default_timeout(30_000)
+    login(page, app_url, next="/")
+    png = _png_file(tmp_path)
+
+    path, _uploads = _send_with_attachment(page, png)
+
+    # Track the image route's fetches from here on — the restored
+    # bubble must load the image by FETCHING the stored path (not an
+    # inline data URL).
+    fetches: list[str] = []
+
+    def _on_request(req: Any) -> None:
+        if "/api/chat-images/" in req.url:
+            fetches.append(req.url)
+
+    page.on("request", _on_request)
+    page.reload()
+    expect(page.locator("#empty-state")).to_be_hidden(timeout=30_000)
+
+    # The restored user bubble carries the image — its src is the
+    # STORED PATH (the record's key), not the live data URL.
+    img = page.locator(".msg.user .msg-image").first
+    expect(img).to_be_visible(timeout=30_000)
+    assert (img.get_attribute("src") or "") == path, "the restore renders from the stored path"
+
+    # The path fetch must actually fire (the lazy img loading it) —
+    # poll with a deadline. ``wait_for_timeout`` (not ``time.sleep``)
+    # is the tick: the sync API dispatches the ``request`` events
+    # queued during it, and a bare sleep would starve the listener.
+    deadline = time.monotonic() + 10
+    while not any(u.rstrip("/").endswith(path) for u in fetches):
+        if time.monotonic() > deadline:
+            raise AssertionError(
+                f"no fetch of the stored path ({len(fetches)} image requests: {fetches!r})"
+            )
+        page.wait_for_timeout(100)
+
+    # The rest of the conversation is unchanged.
+    expect(page.locator(".msg.user .bubble")).to_have_count(1)
+    expect(page.locator(".msg.user .bubble")).to_contain_text(QUESTION)
+    expect(page.locator(".msg.brain .bubble")).to_have_count(1)
+    expect(page.locator(".msg.brain .bubble")).to_contain_text(
+        re.compile(DEFLECT_PHRASE, re.IGNORECASE)
+    )
+
+    # Cleanup.
+    cookies = _admin_cookies(page)
+    row = _wait_saved_row(app_url, cookies, _auto_title(QUESTION))
+    _delete_row(app_url, cookies, row["id"])
+
+
+# ---------------------------------------------------------------------------
+# 4. Share: a fresh anonymous context sees the user's image on the
+#    shared page (the public serve route — the shared view is faithful)
+# ---------------------------------------------------------------------------
+
+
+def test_shared_page_shows_the_user_image(
+    page: Page, browser, app_url: str, mock_llm: int, db_ready: None, tmp_path: Path
+) -> None:
+    _reset_db(mock_llm, seed=False)
+    page.set_default_timeout(30_000)
+    login(page, app_url, next="/")
+    png = _png_file(tmp_path)
+
+    path, _uploads = _send_with_attachment(page, png)
+    cookies = _admin_cookies(page)
+    row = _wait_saved_row(app_url, cookies, _auto_title(QUESTION))
+
+    # The saved row's user record carries the PATH (the share's source
+    # of truth — A5: never base64).
+    detail = httpx.get(f"{app_url}/api/chats/{row['id']}", timeout=10, cookies=cookies)
+    assert detail.status_code == 200
+    saved_user = detail.json()["messages"][0]
+    assert saved_user["image"] == path
+
+    # Share (the chat page's pill — the owner-locked one action):
+    # grant the clipboard so the copy path runs (the status line is
+    # the assertion surface).
+    page.context.grant_permissions(
+        ["clipboard-read", "clipboard-write"], origin=app_url
+    )
+    page.locator("#share-chat-btn").click()
+    expect(page.locator("#send-status")).to_have_text("Share link copied.", timeout=15_000)
+
+    row = _find_row(_chats(app_url, cookies), _auto_title(QUESTION))
+    assert row is not None and row.get("share_url")
+    share_url: str = row["share_url"]
+    assert SHARE_URL_RE.fullmatch(share_url)
+    try:
+        # A FRESH context (no cookies, no localStorage): the shared
+        # page renders the user's image (public route, same bubble
+        # treatment — alt = the record's text).
+        anon = browser.new_context()
+        try:
+            anon_page = anon.new_page()
+            anon_page.goto(app_url + share_url)
+            anon_img = anon_page.locator(".msg.user .msg-image").first
+            expect(anon_img).to_be_visible(timeout=30_000)
+            assert (anon_img.get_attribute("src") or "") == path
+            # The answer text is there too (the shared view is the
+            # full conversation, read-only).
+            expect(anon_page.locator(".msg.brain .bubble")).to_contain_text(
+                re.compile(DEFLECT_PHRASE, re.IGNORECASE)
+            )
+        finally:
+            anon.close()
+    finally:
+        _delete_row(app_url, cookies, row["id"])
+
+
+# ---------------------------------------------------------------------------
+# 5. Default-off negative: the control stays hidden; an API request
+#    with an image gets the hinted error frame, with NO model call
+# ---------------------------------------------------------------------------
+
+
+def _post_chat_sse(
+    app_url: str, cookies: dict[str, str], body: dict[str, Any]
+) -> list[dict[str, Any]]:
+    """``POST /api/chat`` straight from the test process (the hand-
+    crafted request the absent composer control would otherwise make)."""
+    frames: list[dict[str, Any]] = []
+    with httpx.stream(
+        "POST", f"{app_url}/api/chat", json=body, cookies=cookies, timeout=30
+    ) as r:
+        assert r.status_code == 200, r.read()
+        buf = ""
+        for part in r.iter_text():
+            buf += part
+            while "\n\n" in buf:
+                frame, buf = buf.split("\n\n", 1)
+                frame = frame.strip()
+                if frame.startswith("data:"):
+                    frames.append(json.loads(frame.removeprefix("data:").strip()))
+    return frames
+
+
+def test_flag_off_hides_the_control_and_rejects_the_request(
+    page: Page,
+    default_app_url: str,
+    mock_llm: int,
+    db_ready: None,
+) -> None:
+    _reset_db(mock_llm, seed=False)
+    page.set_default_timeout(30_000)
+    login(page, default_app_url, next="/")
+
+    # The config says images off — and the control stays hidden for
+    # GOOD (the default-off contract: the static markup ships hidden,
+    # the reveal gate never fires, the rendered DOM is pre-phase).
+    cfg = httpx.get(f"{default_app_url}/api/config", timeout=10).json()
+    assert cfg["images"] is False
+    expect(page.locator("#attach-btn")).to_be_hidden()
+    expect(page.locator("#attach-file")).to_be_hidden()
+    expect(page.locator("#attach-preview")).to_be_hidden()
+
+    # The server-side contract (the API is the authority — a hand-
+    # crafted request with an image): the phase-114 error frame with
+    # the EXACT detail + hint, ONE terminal frame (no ``done``), and
+    # ZERO model calls (the capture stays empty — the embed never ran).
+    _reset_capture(mock_llm)
+    cookies = _admin_cookies(page)
+    frames = _post_chat_sse(
+        default_app_url,
+        cookies,
+        {"message": "What is in this image?", "image": "/api/chat-images/" + "b" * 32 + ".png"},
+    )
+    assert [f["type"] for f in frames] == ["error"]
+    assert frames[0] == {
+        "type": "error",
+        "detail": "Image support is turned off on this server.",
+        "hint": "Enable BOR_IMAGES in the server's .env (and restart) to ask with an image.",
+    }
+    assert _captured(mock_llm) == []  # no model call (the rejected turn)

tests/e2e/test_security_headers.py

@@ -33,8 +33,13 @@ import re
 
 from playwright.sync_api import ConsoleMessage, Page, expect
 
-#: The exact owner-approved policy (phase 82, decision A1).
+#: The exact owner-approved policy (phase 82, decision A1), with the
-CSP = "default-src 'self'; base-uri 'none'; frame-ancestors 'none'"
+#: phase-123 img-src carve-out (the question-image composer's data-URL
+#: preview + live bubble — ``data:`` is allowed for images ONLY).
+CSP = (
+    "default-src 'self'; base-uri 'none'; frame-ancestors 'none'; "
+    "img-src 'self' data:"
+)
 
 #: Chromium reports CSP denials to the console with this phrasing
 #: ("Refused to … because it violates the following Content Security

tests/integration/test_chat_api.py

@@ -11,7 +11,9 @@ Requires:  podman compose up -d db
 from __future__ import annotations
 
 import asyncio
+import base64
 import hashlib
+import io
 import json
 import logging
 import math
@@ -29,6 +31,7 @@ from sqlalchemy import delete, func, select, text
 from sqlalchemy.orm import Session
 
 from app.api import chat as chat_api
+from app.api import chat_images
 from app.config import Settings, get_settings
 from app.main import app as fastapi_app
 from app.models import Chunk, Document, GitSource, QueryLog
@@ -2197,3 +2200,310 @@ def test_text_only_grounded_turn_frame_has_no_image_url_key_anywhere(
     ]
     for ref in done["sources"] + done["related"]:
         assert set(ref) == {"source", "path", "title"}  # the pre-122 key set
+
+
+# ---------------------------------------------------------------------------
+# Phase 123 (task 01): image questions — the upload → chat flow delivers
+# the multimodal user message to the model (both construction sites), the
+# toggle-off / stale frames settle before any model call (no record),
+# text-only turns stay byte-identical, and the saved/shared chat round-
+# trips the stored PATH (never base64 — LOCKED A5).
+# ---------------------------------------------------------------------------
+
+#: A real 1×1 transparent PNG (the phase-122 fixture bytes) — the server
+#: is content-agnostic (the extension + size gates only), but a well-
+#: formed fixture keeps the data-URL pin honest.
+PNG_1X1 = base64.b64decode(
+    "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAAC0lEQVR4nGP4DwQACfsD/fteaysAAAAASUVORK5CYII="
+)
+
+
+@pytest.fixture()
+def chat_image_store(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> Path:
+    """Point the question-image store (the upload/serve pair) AND the
+    turn pipeline at a tmp dir, with the ``images`` toggle ON — the
+    env-calibrated settings (the conftest mock thresholds) plus the
+    phase-123 pair (``images`` + ``chat_image_dir``); the monkeypatch
+    fixture reverts both patches."""
+    store = tmp_path / "chat-images"
+    store.mkdir()
+    settings = Settings(
+        _env_file=None,  # pyright: ignore[reportCallIssue]
+        images=True,
+        chat_image_dir=str(store),
+    )
+    monkeypatch.setattr(chat_images, "get_settings", lambda: settings)
+    monkeypatch.setattr(chat_api, "get_settings", lambda: settings)
+    return store
+
+
+def _upload_image(client: TestClient, name: str = "screenshot.png") -> str:
+    """One question-image upload (the composer's step before send) —
+    returns the served path (the value the chat request accepts)."""
+    r = client.post(
+        "/api/chat-images",
+        files={"file": (name, io.BytesIO(PNG_1X1), "image/png")},
+    )
+    assert r.status_code == 200, r.text
+    return r.json()["path"]
+
+
+def _stream_chat_with(
+    client: TestClient, body: dict[str, Any]
+) -> tuple[int, str, list[dict[str, Any]]]:
+    """``_stream_chat`` with an arbitrary body (the ``image`` key)."""
+    with client.stream("POST", "/api/chat", json=body) as r:
+        assert r.status_code == 200
+        assert r.headers["content-type"].startswith("text/event-stream")
+        buf = ""
+        frames: list[dict[str, Any]] = []
+        for part in r.iter_text():
+            buf += part
+            while "\n\n" in buf:
+                frame, buf = buf.split("\n\n", 1)
+                frame = frame.strip()
+                if frame.startswith("data:"):
+                    frames.append(json.loads(frame.removeprefix("data:").strip()))
+        assert buf.strip() == "", "stream must end on a frame boundary"
+    return r.status_code, r.headers["content-type"], frames
+
+
+def _expected_image_content(question: str) -> list[dict[str, Any]]:
+    """The multimodal user content list the model must receive for a
+    question that carried the fixture image (the text part + the
+    image_url part — a data URL built server-side from the stored bytes
+    + the phase-122 mime map)."""
+    return [
+        {"type": "text", "text": question},
+        {
+            "type": "image_url",
+            "image_url": {
+                "url": f"data:image/png;base64,{base64.b64encode(PNG_1X1).decode('ascii')}"
+            },
+        },
+    ]
+
+
+def test_image_turn_delivers_the_multimodal_user_message(
+    client, db, seeded_kb: FakeRagLLM, chat_image_store: Path
+) -> None:
+    """The full flow (LOCKED A5): the client uploads FIRST, then the
+    turn request carries the returned path — and the GROUNDED branch
+    (construction site 2: ``run_agent`` builds its own ``[system,
+    *history, user]`` from the value chat.py passes — the pinned flow)
+    delivers the multimodal content list to the model: the text part +
+    the image_url data URL that decodes to the stored bytes."""
+    fastapi_app.dependency_overrides[chat_api.get_llm] = lambda: seeded_kb
+    try:
+        path = _upload_image(client)
+        _, _, frames = _stream_chat_with(
+            client, {"message": QUESTION, "image": path}
+        )
+    finally:
+        fastapi_app.dependency_overrides.clear()
+
+    assert frames[-1]["type"] == "done"
+    assert frames[-1]["deflected"] is False
+    assert len(seeded_kb.seen_messages) == 1
+    assert seeded_kb.seen_messages[0][-1] == {
+        "role": "user",
+        "content": _expected_image_content(QUESTION),
+    }
+    # the data URL really is the stored bytes (decode + compare)
+    url = seeded_kb.seen_messages[0][-1]["content"][1]["image_url"]["url"]
+    assert base64.b64decode(url.split(",", 1)[1]) == PNG_1X1
+
+
+def test_deflected_image_turn_delivers_the_multimodal_user_message(
+    client, db, seeded_kb: FakeRagLLM, chat_image_store: Path
+) -> None:
+    """Construction site 1 (the deflected branch consumes chat.py's
+    ``messages`` list directly): an off-topic question + image still
+    delivers the SAME multimodal list — the LOW prompt path never
+    drops the attachment."""
+    fastapi_app.dependency_overrides[chat_api.get_llm] = lambda: seeded_kb
+    try:
+        path = _upload_image(client)
+        _, _, frames = _stream_chat_with(
+            client, {"message": OFF_TOPIC, "image": path}
+        )
+    finally:
+        fastapi_app.dependency_overrides.clear()
+
+    assert frames[-1]["type"] == "done"
+    assert frames[-1]["deflected"] is True
+    assert len(seeded_kb.seen_messages) == 1
+    assert seeded_kb.seen_messages[0][-1] == {
+        "role": "user",
+        "content": _expected_image_content(OFF_TOPIC),
+    }
+
+
+def test_image_turn_with_toggle_off_yields_the_hinted_frame_and_calls_nothing(
+    client, db, seeded_kb: FakeRagLLM, chat_image_store: Path, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """The ``BOR_IMAGES`` gate: off with an image set → the phase-114
+    error frame with the EXACT detail + hint (ONE terminal frame — no
+    ``done``), and NO model call (zero embeds, zero requests) and NO
+    record (the rejected turn saves nothing — the existing error-path
+    convention)."""
+    monkeypatch.setattr(
+        chat_api,
+        "get_settings",
+        lambda: Settings(
+            _env_file=None,  # pyright: ignore[reportCallIssue]
+            images=False,
+            chat_image_dir=str(chat_image_store),
+        ),
+    )
+    fastapi_app.dependency_overrides[chat_api.get_llm] = lambda: seeded_kb
+    try:
+        path = _upload_image(client)
+        _, _, frames = _stream_chat_with(
+            client, {"message": "What is in this image?", "image": path}
+        )
+    finally:
+        fastapi_app.dependency_overrides.clear()
+
+    assert [f["type"] for f in frames] == ["error"]
+    assert frames[0] == {
+        "type": "error",
+        "detail": "Image support is turned off on this server.",
+        "hint": "Enable BOR_IMAGES in the server's .env (and restart) to ask with an image.",
+    }
+    # NO model call: the QUESTION embed never ran (``question_embeds``
+    # counts ``embed_one`` calls — the import's batch embeds are a
+    # different counter) and the answer endpoint was never asked.
+    assert seeded_kb.question_embeds == []
+    assert seeded_kb.seen_messages == []
+    assert db.scalars(select(QueryLog)).all() == []  # NO query_log row
+
+
+def test_image_turn_with_a_missing_stored_file_yields_the_stale_frame(
+    client, db, seeded_kb: FakeRagLLM, chat_image_store: Path
+) -> None:
+    """The stale-path edge (the file was deleted out-of-band): the SAME
+    frame shape with the "no longer available" detail and NO hint (the
+    banner's default copy is the honest fallback) — again before any
+    model call, no record."""
+    fastapi_app.dependency_overrides[chat_api.get_llm] = lambda: seeded_kb
+    try:
+        stale = "/api/chat-images/" + "e" * 32 + ".png"  # well-formed, absent
+        _, _, frames = _stream_chat_with(
+            client, {"message": "What is in this image?", "image": stale}
+        )
+    finally:
+        fastapi_app.dependency_overrides.clear()
+
+    assert [f["type"] for f in frames] == ["error"]
+    assert frames[0] == {
+        "type": "error",
+        "detail": "That image is no longer available.",
+        "hint": None,
+    }
+    assert seeded_kb.question_embeds == []  # NO model call (see the toggle-off test)
+    assert seeded_kb.seen_messages == []
+    assert db.scalars(select(QueryLog)).all() == []
+
+
+def test_text_only_turn_is_byte_identical_with_images_enabled(
+    client, db, seeded_kb: FakeRagLLM, chat_image_store: Path
+) -> None:
+    """``image=None`` with the toggle ON: the user message is the PLAIN
+    STRING (not a content list) — the multimodal branch is inert, and
+    the turn behaves exactly as pre-phase (done frame, the question
+    embedded whole)."""
+    fastapi_app.dependency_overrides[chat_api.get_llm] = lambda: seeded_kb
+    try:
+        _, _, frames = _stream_chat_with(client, {"message": QUESTION})
+    finally:
+        fastapi_app.dependency_overrides.clear()
+
+    assert frames[-1]["type"] == "done"
+    assert seeded_kb.seen_messages[0][-1] == {"role": "user", "content": QUESTION}
+    assert isinstance(seeded_kb.seen_messages[0][-1]["content"], str)
+    assert seeded_kb.question_embeds == [QUESTION[: 1200]]
+
+
+def test_saved_chat_round_trips_the_user_image_path(
+    client, db, chat_image_store: Path
+) -> None:
+    """Persistence (LOCKED A5): the user record carries the stored
+    PATH — the stored JSONB and the saved-chat response round-trip it,
+    the brain record carries NO image key, and NOTHING base64 crosses
+    the storage boundary. A text-only record stays without the key
+    (the phase-50 byte-identical contract for text-only chats)."""
+    db.execute(text("TRUNCATE saved_chats"))
+    db.commit()
+    try:
+        path = _upload_image(client)
+        r = client.post(
+            "/api/chats",
+            json={
+                "messages": [
+                    {"who": "user", "text": "What is in this image?", "image": path},
+                    {"who": "brain", "text": "A cat, by the look of it."},
+                ]
+            },
+        )
+        assert r.status_code == 201, r.text
+        body = r.json()
+        assert body["messages"][0]["image"] == path
+        assert "image" not in body["messages"][1]  # brain records never carry it
+
+        # The RAW stored JSONB: the path, never base64 (LOCKED A5)
+        raw = db.execute(
+            text("SELECT messages FROM saved_chats WHERE id = :id"),
+            {"id": body["id"]},
+        ).scalar_one()
+        assert raw[0]["image"] == path
+        assert "base64" not in json.dumps(raw)
+
+        # The admin GET round-trips it losslessly
+        got = client.get(f"/api/chats/{body['id']}")
+        assert got.status_code == 200
+        assert got.json()["messages"][0]["image"] == path
+        assert "image" not in got.json()["messages"][1]
+    finally:
+        db.execute(text("TRUNCATE saved_chats"))
+        db.commit()
+
+
+def test_shared_chat_serves_the_user_image_path(
+    client, db, chat_image_store: Path
+) -> None:
+    """The shared view is faithful: the public snapshot carries the
+    user's image path (the public ``messages`` shape already includes
+    the optional key), and the image bytes themselves are publicly
+    servable (the image is part of the chat's content — phase 55 A1)."""
+    db.execute(text("TRUNCATE saved_chats"))
+    db.commit()
+    try:
+        path = _upload_image(client)
+        r = client.post(
+            "/api/chats",
+            json={
+                "share": True,
+                "messages": [
+                    {"who": "user", "text": "What is in this image?", "image": path},
+                    {"who": "brain", "text": "A cat, by the look of it."},
+                ],
+            },
+        )
+        assert r.status_code == 201, r.text
+        share_url = r.json()["share_url"]
+        token = share_url.rsplit("/", 1)[-1]
+
+        anon = TestClient(fastapi_app)
+        got = anon.get(f"/api/shared/{token}")
+        assert got.status_code == 200
+        messages = got.json()["messages"]
+        assert messages[0]["image"] == path
+        assert "image" not in messages[1]
+
+        img = anon.get(path)
+        assert img.status_code == 200
+        assert img.content == PNG_1X1
+    finally:
+        db.execute(text("TRUNCATE saved_chats"))
+        db.commit()

tests/integration/test_chats_api.py

@@ -24,6 +24,7 @@ Requires:  podman compose up -d db
 """
 from __future__ import annotations
 
+import json
 import re
 import time
 import uuid
@@ -799,6 +800,105 @@ def test_public_read_returns_snapshot_without_private_keys(
     assert body["messages"] == _expect([_user(FIRST_QUESTION), FULL_BRAIN])
 
 
+# ---------------------------------------------------------------------------
+# Phase 123 (tasks 03/04): the question's attached image — the saved
+# and shared shape carries the stored PATH (LOCKED A5: never base64),
+# on the USER record only (the attachment belongs to the question — a
+# brain record never carries the key). Text-only records stay WITHOUT
+# the key (absent, never null — the phase-50 byte-identical contract,
+# pinned by ``_expect`` above; the ``ChatMessage`` wrap serializer does
+# the dropping, so every surface — the stored JSONB, the admin GET,
+# the public shared read — inherits it).
+# ---------------------------------------------------------------------------
+
+#: A well-formed stored path (the ``POST /api/chat-images`` response's
+#: shape — the chat-images router names the file
+#: ``<uuid4().hex>.<ext>``; the API boundary itself only bounds the
+#: string to 500 chars, the pattern gate is the chat request's).
+IMAGE_PATH = "/api/chat-images/" + "a" * 32 + ".png"
+
+
+def _user_with_image(text: str) -> dict[str, Any]:
+    return {"who": "user", "text": text, "image": IMAGE_PATH}
+
+
+def test_create_round_trips_the_user_image_path(
+    admin_client: TestClient, db: Session
+) -> None:
+    """The user record carries the PATH at every boundary: the 201
+    body, the RAW stored JSONB (never base64 — the A5 contract), and
+    the admin GET — and the brain record stays WITHOUT the key.
+    A text-only record in the SAME chat stays key-free too."""
+    r = admin_client.post(
+        "/api/chats",
+        json={
+            "messages": [
+                _user(FIRST_QUESTION),  # text-only — stays WITHOUT the key
+                _user_with_image("What is in this image?"),
+                {"who": "brain", "text": "A cat, by the look of it."},
+            ]
+        },
+    )
+    assert r.status_code == 201, r.text
+    body = r.json()
+    assert "image" not in body["messages"][0]
+    assert body["messages"][1]["image"] == IMAGE_PATH
+    assert "image" not in body["messages"][2]
+
+    # The RAW stored JSONB (the DB is the durable boundary — the
+    # served bodies could in principle re-derive it): the path, and
+    # NOTHING base64 anywhere in the payload.
+    raw = db.execute(
+        text("SELECT messages FROM saved_chats WHERE id = :id"),
+        {"id": body["id"]},
+    ).scalar_one()
+    assert "image" not in raw[0]
+    assert raw[1]["image"] == IMAGE_PATH
+    assert "image" not in raw[2]
+    assert "base64" not in json.dumps(raw)
+
+    got = admin_client.get(f"/api/chats/{body['id']}")
+    assert got.status_code == 200
+    assert "image" not in got.json()["messages"][0]
+    assert got.json()["messages"][1]["image"] == IMAGE_PATH
+    assert "image" not in got.json()["messages"][2]
+
+
+def test_shared_serve_includes_the_user_image_path(
+    admin_client: TestClient,
+) -> None:
+    """The shared view is faithful (task 03's pin): the PUBLIC
+    snapshot's user record carries the image path — the public
+    ``messages`` shape already gains the one optional key, so no new
+    shared-shape field exists — and the brain / text-only records
+    stay WITHOUT it. The image bytes themselves ride the public
+    serve route (phase 55 A1 — the image is part of the chat's
+    content, the token is the credential): pinned in
+    ``test_chat_api.py`` alongside the upload."""
+    r = admin_client.post(
+        "/api/chats",
+        json={
+            "messages": [
+                _user(FIRST_QUESTION),  # text-only — stays WITHOUT the key
+                _user_with_image("What is in this image?"),
+                {"who": "brain", "text": "A cat, by the look of it."},
+            ]
+        },
+    )
+    assert r.status_code == 201, r.text
+    share_url = _share(admin_client, r.json()["id"])["share_url"]
+
+    anon = TestClient(fastapi_app)  # fresh jar: truly anonymous
+    got = anon.get(f"/api{share_url}")
+    assert got.status_code == 200
+    body = got.json()
+    assert set(body) == SHARED_OUT_KEYS  # no new shared-shape field
+    messages = body["messages"]
+    assert "image" not in messages[0]
+    assert messages[1]["image"] == IMAGE_PATH
+    assert "image" not in messages[2]
+
+
 def test_public_read_wrong_and_revoked_tokens_404_with_one_detail(
     admin_client: TestClient,
 ) -> None:

tests/integration/test_security_headers.py

@@ -8,7 +8,11 @@ API JSON, static assets, even the static catch-all's 404s — carries:
 
 * ``Content-Security-Policy`` — the exact A1 string (``default-src 'self';
   base-uri 'none'; frame-ancestors 'none'`` → clickjacking closed, no
-  inline anything because the No-CDN frontend has none);
+  inline anything because the No-CDN frontend has none), extended by
+  the phase-123 ``img-src 'self' data:`` carve-out (the question-image
+  composer's data-URL preview + live bubble — see ``CSP`` in
+  ``app/core/security_headers.py``; the ``data:`` allowance is scoped
+  to img-src only);
 * ``X-Frame-Options: DENY`` — the legacy no-framing fallback;
 * ``X-Content-Type-Options: nosniff`` — the MIME-confusion belt.
 
@@ -69,9 +73,7 @@ def test_page_carries_all_three_headers(client: TestClient, db: Session) -> None
     response = client.get("/")
     assert response.status_code == 200
     _assert_security_headers(response)
-    assert response.headers["content-security-policy"] == (
+    assert response.headers["content-security-policy"] == CSP
-        "default-src 'self'; base-uri 'none'; frame-ancestors 'none'"
-    )
 
 
 def test_api_health_carries_all_three_headers(client: TestClient) -> None:

tests/unit/test_chat_persistence.py

@@ -126,10 +126,24 @@ def test_raw_text_only_stored_and_re_rendered_on_restore() -> None:
 def test_save_points_user_on_send_and_brain_on_done() -> None:
     """Save points: the user message is stored the moment it is sent (BEFORE
     the fetch — a failed turn keeps the question); the brain message is
-    stored on `done` with the done metadata (sources/deflected/suggestions)."""
+    stored on `done` with the done metadata (sources/deflected/suggestions).
+
+    Phase 123 (task 02): the user push is conditional — the record gains
+    the optional `image` key (the STORED path from the upload step,
+    A5: never base64) only when an attachment exists; the text-only
+    branch is the pre-phase object verbatim. The save point (push +
+    save before the turn starts) is the contract."""
     js = _js()
-    user_push = js.find('conversation.push({ who: "user", text })')
+    run_turn = js.find("async function runTurn")
-    assert user_push != -1
+    assert run_turn != -1, "runTurn must exist (the phase-49 extraction)"
+    user_push = js.find("conversation.push(", run_turn)
+    push_block = js[user_push : js.find("saveConversation()", user_push)]
+    assert '{ who: "user", text, image: image.path }' in push_block, (
+        "an attached question stores the image path (A5)"
+    )
+    assert '{ who: "user", text }' in push_block, (
+        "a text-only question keeps the pre-phase record shape"
+    )
     assert user_push < js.find('fetch("/api/chat"'), (
         "the user message must be saved before the turn starts"
     )

tests/unit/test_frontend_feedback.py

@@ -378,15 +378,22 @@ def test_composer_form_is_novalidate() -> None:
 def test_run_turn_is_the_extracted_turn_handler() -> None:
     """Phase 49 (owner-locked 2026-08-29, TODO.md L4): the turn
     machinery is extracted from handleSend into
-    `runTurn(text, { reask = false })`. handleSend keeps only the
+    `runTurn(text, { reask = false, image = null })` (the `image`
-    form-level pre-work (the in-flight stop guard, the !text guard, the
+    argument is phase 123 task 02's optional attachment). handleSend
-    composer pre-work) and delegates; the user append + persistence
+    keeps the form-level pre-work (the in-flight stop guard, the
-    save point 1 (push + save) sit in runTurn's `!reask` block — the
+    !text guard, the composer pre-work) plus — since phase 123 — the
-    redo-in-place retry path skips both, because the question is
+    locked-A8 upload step (an attached image uploads BEFORE the
-    already in the DOM and in `conversation`."""
+    input is cleared; a failed upload blocks the send) and delegates;
+    the user append + persistence save point 1 (push + save) sit in
+    runTurn's `!reask` block — the redo-in-place retry path skips
+    both, because the question is already in the DOM and in
+    `conversation`."""
     js = _js()
-    assert re.search(r"async function runTurn\(text, \{ reask = false \} = \{\}\)", js), (
+    assert re.search(
-        "runTurn(text, { reask = false }) must be the extracted turn handler"
+        r"async function runTurn\(text, \{ reask = false, image = null \} = \{\}\)", js
+    ), (
+        "runTurn(text, { reask = false, image = null }) must be the extracted "
+        "turn handler"
     )
     handle = js.find("async function handleSend")
     turn = js.find("async function runTurn")
@@ -397,7 +404,12 @@ def test_run_turn_is_the_extracted_turn_handler() -> None:
     assert 'input.value = ""' in handle_body
     assert "autoGrow()" in handle_body
     assert "clearErrorBanner()" in handle_body
-    assert "runTurn(text, { reask: false })" in handle_body, ("handleSend delegates the turn")
+    # Phase 123 (task 02, locked A8): the delegation carries the
+    # upload step's `image` ({ path, src, alt } | null) — null for a
+    # text-only send (the pre-phase shape).
+    assert "runTurn(text, { reask: false, image })" in handle_body, (
+        "handleSend delegates the turn (with the attached image's path)"
+    )
     assert 'addMessage("user"' not in handle_body, (
         "the user append moved with the turn into runTurn"
     )
@@ -412,8 +424,21 @@ def test_run_turn_is_the_extracted_turn_handler() -> None:
     )
     turn_top = js[turn:wrap_idx]
     assert "if (!reask) {" in turn_top, "the reask gate guards the append + push"
-    assert 'addMessage("user", renderMarkdown(text), true)' in turn_top
+    # Phase 123 (task 02): the user append + push carry the optional
-    assert 'conversation.push({ who: "user", text })' in turn_top
+    # attachment — the bubble gets { src, alt } (the data URL live; the
+    # stored path is the fallback) and the record gains the `image`
+    # key (the STORED path — A5: never base64) only when one exists;
+    # a null image keeps the pre-phase shapes verbatim. The strip must
+    # not linger into the turn (cleared after the bubble renders).
+    assert re.search(
+        r'addMessage\(\s*"user",\s*renderMarkdown\(text\),\s*true', turn_top
+    ), "the submit must reveal the user message (scroll intent true)"
+    assert "image ? { src: image.src || image.path, alt: image.alt } : null" in turn_top
+    assert "{ who: \"user\", text, image: image.path }" in turn_top
+    assert "{ who: \"user\", text }" in turn_top
+    assert "clearAttachedImage()" in turn_top, (
+        "the preview strip must not linger into the turn"
+    )
     assert "saveConversation()" in turn_top
 
 

tests/unit/test_frontend_scroll.py

@@ -93,12 +93,16 @@ def test_scroll_helper_is_unconditional() -> None:
 
 
 def test_add_message_takes_explicit_scroll_intent() -> None:
-    """addMessage(who, html, scroll = false): the phase-18
+    """addMessage(who, html, scroll = false, image = null): the phase-18
     scrollBehavior/force parameters are gone; the bubble scrolls only
-    when the caller explicitly asks (submit reveal, restore landing)."""
+    when the caller explicitly asks (submit reveal, restore landing).
+    Phase 123 (task 02) appended the optional `image` argument (the
+    question's attached image — { src, alt } on a user bubble, the ONE
+    renderer for live + restore + shared); the scroll contract is
+    untouched."""
     js = _js()
     body = _fn_body(js, "addMessage")
-    assert "function addMessage(who, html, scroll = false)" in body
+    assert "function addMessage(who, html, scroll = false, image = null)" in body
     assert "if (scroll) scrollReveal(wrap)" in body
     assert "force" not in body
     assert "scrollBehavior" not in body
@@ -119,9 +123,13 @@ def test_submit_reveals_user_message() -> None:
     assert turn != -1, "runTurn must exist (phase 49 extraction)"
     body = js[turn : js.find("\n}\n", turn)]
     assert "if (!reask) {" in body, "the user append is gated on !reask"
-    assert 'addMessage("user", renderMarkdown(text), true)' in body, (
+    # Phase 123 (task 02): the user append gained the optional image
-        "the submit must reveal the user message (scroll intent true)"
+    # argument (the attached image's { src, alt }) — the call is
-    )
+    # multi-line now; the contract is the same: user + the raw text +
+    # the explicit scroll intent true.
+    assert re.search(
+        r'addMessage\(\s*"user",\s*renderMarkdown\(text\),\s*true', body
+    ), "the submit must reveal the user message (scroll intent true)"
     for call in re.findall(r'addMessage\("brain"([^)]*)\)', body):
         assert "true" not in call, (
             f"streaming brain bubbles must not scroll the page: {call!r}"
@@ -168,7 +176,16 @@ def test_restore_landing_is_one_shot() -> None:
     assert 'addMessage("brain", renderMarkdown(m.text), true)' in body
     assert js.count('"auto", true') == 0, "the old forced 'auto' landing must be gone"
     # Submit reveal + the two restore landings — nothing else scrolls.
-    assert js.count(", true)") == 3, "only submit + the two restore calls may scroll"
+    # Phase 123 (task 02): the submit call is multi-line (the optional
+    # image argument follows the scroll intent), so it no longer ends
+    # in the single-line ", true)" literal — the two restore calls do;
+    # the submit reveal is counted by its own (multi-line) shape.
+    assert js.count(", true)") == 2, (
+        "only the two restore calls may scroll (single-line shape)"
+    )
+    assert len(re.findall(r'addMessage\(\s*"user",\s*renderMarkdown\(text\),\s*true', js)) == 1, (
+        "the submit reveal may scroll (multi-line since phase 123's image argument)"
+    )
     # The marker comment documents the one-shot, load-time contract.
     assert "restore landing" in body
     assert "one-shot" in body

tests/unit/test_pinned_composer.py

@@ -313,9 +313,11 @@ def test_chat_bottom_unit_is_last_child_of_the_chat_shell() -> None:
     `.chat-shell` is the `.chat-bottom` wrapper — NO id (nothing in JS
     binds it; the bindings live on the inner elements, the move is pure
     HTML/CSS) — holding the `.chat-actions` row, the phase-104
-    `#char-count` counter, and the `#composer` form, in that order: the
+    `#char-count` counter, the phase-123 `#attach-preview` strip (hidden
-    row + counter + composer are ONE sticky unit, and the wrapper owns
+    by default — zero height at rest, the sticky geometry untouched),
-    the shell's bottom slot, so the sticky shift range is still that
+    and the `#composer` form, in that order: the row + counter +
+    preview + composer are ONE sticky unit, and the wrapper owns the
+    shell's bottom slot, so the sticky shift range is still that
     column's box (a sibling after it would carve the range away and
     re-break the pin). The composer form keeps `novalidate` and its
     contract ids."""
@@ -331,11 +333,12 @@ def test_chat_bottom_unit_is_last_child_of_the_chat_shell() -> None:
         "elements"
     )
     kids = last["children"]
-    assert len(kids) == 3, (
+    assert len(kids) == 4, (
-        "the unit holds exactly three element children: .chat-actions, "
+        "the unit holds exactly four element children: .chat-actions, "
-        "then #char-count (phase 104), then #composer"
+        "then #char-count (phase 104), then #attach-preview (phase 123), "
+        "then #composer"
     )
-    row, counter, form = kids
+    row, counter, preview, form = kids
     assert row["tag"] == "div" and (
         row["attrs"].get("class") or ""
     ).split() == ["chat-actions"], (
@@ -354,6 +357,18 @@ def test_chat_bottom_unit_is_last_child_of_the_chat_shell() -> None:
         "the counter ships hidden — it appears only from 80% of the "
         "4,000-char cap (app.js updateCharCount)"
     )
+    # Phase 123 (task 02, TODO L6): the attach preview strip — a
+    # hidden-by-default div between the counter and the composer (the
+    # selected image above the input row; zero height while hidden, the
+    # pinned-cluster geometry untouched).
+    assert preview["tag"] == "div" and (
+        preview["attrs"].get("id") == "attach-preview"
+    ), "the third child is the phase-123 #attach-preview strip"
+    assert (preview["attrs"].get("class") or "") == "attach-preview"
+    assert "hidden" in preview["attrs"], (
+        "the strip ships hidden — it appears only while a file is "
+        "attached (app.js attachedImage)"
+    )
     assert form["tag"] == "form" and form["attrs"].get("id") == "composer"
     assert "novalidate" in form["attrs"], (
         "phase 48: the composer form stays `novalidate` (a `required` "

tests/unit/test_save_chat_ui.py

@@ -696,11 +696,11 @@ def test_chat_actions_wrapper_holds_both_pills_in_order() -> None:
     from the top of the column to the bottom: below the ``#messages``
     section, directly above the composer; nothing but the row's own
     comment lands between ``#messages`` and the row, and nothing but the
-    phase-104 ``#char-count`` counter + the composer comment lands
+    phase-104 ``#char-count`` counter + the phase-123 attach preview
-    between the row and the composer (the counter is hidden by default —
+    strip + the composer comment lands between the row and the composer
-    zero height, the pinned-cluster geometry untouched). No
+    (both hidden by default — zero height at rest, the pinned-cluster
-    other page carries ``.chat-actions`` (chat-page only, like the
+    geometry untouched). No other page carries ``.chat-actions``
-    pills)."""
+    (chat-page only, like the pills)."""
     html = _index()
     start = html.find('<div class="chat-actions">')
     assert start != -1, "index.html must carry the .chat-actions wrapper"
@@ -734,8 +734,20 @@ def test_chat_actions_wrapper_holds_both_pills_in_order() -> None:
     after = html[end:composer_idx]
     # Phase 104 (owner 2026-09-12): the ONE permitted child between the
     # row and the composer is the hidden-by-default question-length
-    # counter — everything else (ids, buttons, sections, forms) is
+    # counter; phase 123 (task 02, TODO L6) added the second — the
-    # still excluded from the gap.
+    # attach preview strip (the selected image above the input row:
+    # thumbnail + filename + remove button), also `hidden` by default
+    # (the global [hidden] rule — zero height at rest, the
+    # pinned-cluster geometry untouched). Everything else (ids,
+    # buttons, sections, forms) is still excluded from the gap — the
+    # strip's own element block is stripped (like the counter) so the
+    # exclusions below stay meaningful.
+    strip_start = after.find('<div class="attach-preview"')
+    assert strip_start != -1, (
+        "the phase-123 attach preview strip sits above the composer"
+    )
+    strip_end = after.find("</div>", strip_start) + len("</div>")
+    after = after[:strip_start] + after[strip_end:]
     after_minus_counter = after.replace(
         '<p class="char-count" id="char-count" hidden></p>', ""
     )
@@ -746,8 +758,9 @@ def test_chat_actions_wrapper_holds_both_pills_in_order() -> None:
         and "<section" not in after_minus_counter
         and "<form" not in after_minus_counter
     ), (
-        "nothing but the phase-104 counter + the composer comment lands "
+        "nothing but the phase-104 counter + the phase-123 attach "
-        "between the row and the composer"
+        "preview + the composer comment lands between the row and the "
+        "composer"
     )
     # Phase 76 (task 02): the folded view files are gone (the shell's
     # chat view is the one and only carrier of the row — pinned above);

tests/unit/test_security_headers.py

@@ -29,7 +29,10 @@ from app.core.security_headers import CSP, SecurityHeadersMiddleware
 #: The exact expected header set (decision A1 for the CSP, A4 for the
 #: other two).
 EXPECTED_HEADERS = {
-    "content-security-policy": "default-src 'self'; base-uri 'none'; frame-ancestors 'none'",
+    "content-security-policy": (
+        "default-src 'self'; base-uri 'none'; frame-ancestors 'none'; "
+        "img-src 'self' data:"
+    ),
     "x-frame-options": "DENY",
     "x-content-type-options": "nosniff",
 }
@@ -111,10 +114,19 @@ def _assert_security_headers(start: Message, expected_extra: dict[str, str] | No
 
 
 def test_csp_constant_is_the_exact_a1_policy() -> None:
-    """The owner-approved A1 string, verbatim: same-origin default, no
+    """The owner-approved A1 string (phase 82), verbatim, with the
-    base-tag hijack, no framing — no 'unsafe-inline', no report sink."""
+    phase-123 ``img-src`` carve-out (the question-image composer's
-    assert CSP == "default-src 'self'; base-uri 'none'; frame-ancestors 'none'"
+    data-URL preview + live bubble — see ``security_headers.CSP``):
+    same-origin default, no base-tag hijack, no framing — no
+    'unsafe-inline', no report sink, and the ``data:`` allowance is
+    SCOPED to img-src (never script/style/fetch)."""
+    assert CSP == (
+        "default-src 'self'; base-uri 'none'; frame-ancestors 'none'; "
+        "img-src 'self' data:"
+    )
     assert "unsafe-inline" not in CSP
+    # the carve-out is img-src ONLY — no other directive gains data:
+    assert CSP.count("data:") == 1
 
 
 # ---------------------------------------------------------------------------
@@ -158,6 +170,7 @@ def test_pre_existing_csp_from_an_inner_layer_is_preserved() -> None:
     while the other two headers are still added."""
     themed = (
         "default-src 'self'; base-uri 'none'; frame-ancestors 'none'; "
+        "img-src 'self' data:; "
         "style-src 'self' 'sha256-2rm3wPcQfXmE8q1s9vBzK7hN4tY5uJ6gW3oR0cAeDfH='"
     )
     wrapped = SecurityHeadersMiddleware(

tests/unit/test_sources_midstream.py

@@ -101,10 +101,15 @@ def test_persisted_on_leave_flag_is_module_scoped_and_turn_reset() -> None:
 
     # Reset at the top of the turn handler (runTurn — phase 49 extracted
     # the turn from handleSend) — before the turn's fetch, where the
-    # other turn locals are initialized.
+    # other turn locals are initialized. The pin is the ORDER (resets
+    # before the fetch), not a char window: phase 123 task 02 grew the
+    # save-point-1 region above the resets (the attached image's bubble
+    # + record + strip clear) without moving the resets.
     turn = js.find("async function runTurn")
     assert turn != -1
-    top = js[turn : turn + 1500]
+    fetch_idx = js.find('fetch("/api/chat"', turn)
+    assert fetch_idx != -1
+    top = js[turn:fetch_idx]
     assert "persistedOnLeave = false;" in top, (
         "persistedOnLeave must be reset per turn, at the top of the turn handler"
     )