diff --git a/.s2s/BACKLOG.md b/.s2s/BACKLOG.md
index 5c77651f..38e57aea 100644
--- a/.s2s/BACKLOG.md
+++ b/.s2s/BACKLOG.md
@@ -683,9 +683,11 @@ As a result, `conversation.j2` and `TemplateRenderer.render_conversation()` are
 
 ### DEBT-018: Scope widget `--vektra-primary` override and dedupe style node
 
-**Status**: planned | **Priority**: low | **Created**: 2026-04-21
+**Status**: completed | **Priority**: low | **Created**: 2026-04-21 | **Completed**: 2026-04-27 (v0.5.0)
 **Origin**: CodeRabbit review on PR #66 (v0.5.0), `vektra-learn/widget/src/chat-ui.js:138-144`
 
+**Resolution**: `_injectStyles()` now writes the `--vektra-primary` override scoped to `.vektra-chat-btn, .vektra-chat-panel` (no longer to `:root`) and reuses a single `<style id="vektra-primary-override">` element across instantiations.
+
 **Context**: `ChatUI._injectStyles()` appends a new `<style>` element setting `:root { --vektra-primary: <color> }` on every instantiation. Two consequences:
 
 1. Repeated construction (hot reload, multi-instance embedding, host-page re-init) accumulates style nodes.
@@ -722,9 +724,11 @@ In today's deploy there is one widget per page and init fires once, so the impac
 
 ### DEBT-020: Audit log fallback when `request_id` is missing on sensitive endpoints
 
-**Status**: planned | **Priority**: medium | **Created**: 2026-04-26
+**Status**: completed | **Priority**: medium | **Created**: 2026-04-26 | **Completed**: 2026-04-27 (v0.5.0)
 **Origin**: Gemini review on PR #71 (v0.5.0 release), `vektra-admin/src/vektra_admin/api.py:768-783`. Same pattern applies to sensitive reads, e.g. `get_conversation_turns` in `vektra-admin/src/vektra_admin/api.py:491-539`.
 
+**Resolution**: each of `vektra-admin/api.py`, `vektra-learn/api.py`, and `vektra-ingest/api.py` declares a private `_resolve_request_id(request) -> UUID` helper that synthesizes `uuid4()` when `request.state.request_id` is missing and emits a `request_id_middleware_missing_fallback` structlog warning. All known sensitive endpoints (admin api-keys CRUD, namespace config PATCH, admin/learn conversation turns reads, ingest async + direct audit writers) now audit unconditionally. Helper duplication across three modules is intentional for v0.5.0 — extraction to `vektra_shared` is tracked separately if a fourth caller appears.
+
 **Context**: `patch_namespace_config` writes the audit log only when `request.state.request_id` is truthy:
 
 ```python
@@ -781,6 +785,51 @@ Path A is sufficient for the immediate goal (one fewer round-trip). Path B is a
 
 ---
 
+### DEBT-022: Widget multi-instance primary-color and base-style support
+
+**Status**: planned | **Priority**: low | **Created**: 2026-04-27
+**Origin**: Gemini review on PR #73 (v0.5.0 hardening), `vektra-learn/widget/src/chat-ui.js:152`
+
+**Context**: DEBT-018 closed the host-page leak (`:root` → widget-roots scoped) and deduped the `--vektra-primary` override style node. It does **not** support multiple widgets on the same page with different primary colors: the override is keyed by a global `id="vektra-primary-override"` and writes class selectors shared by every instance, so the last constructor to fire wins for all instances. Separately, the main `<style>` block (the theme stylesheet) still appends a fresh element on every `ChatUI` construction — fine for the current 1-widget-per-page assumption, but accumulates under hot-reload or future multi-instance embedding.
+
+Today's deploy is single-instance, so the gap is theoretical. Filing for the moment we ship multi-instance embedding (e.g. an instructor-side admin widget alongside a student widget on the same LMS page).
+
+**Proposed approach**:
+1. Apply per-instance primary color via `style.setProperty("--vektra-primary", color)` on the widget's root elements (`._btn` and `._panel`) inside `_createElements`, instead of writing a global stylesheet override. Drop the `vektra-primary-override` style node.
+2. Dedupe the main style block too: look up `document.getElementById("vektra-chat-ui-styles")` and reuse if present; otherwise create. Note: instances must agree on theme — or theme should also become per-instance.
+3. Decide whether `--vektra-primary` lookups inside descendants (`.vektra-chat-msg.user`, etc.) still resolve correctly via cascade after the per-instance set.
+
+**Acceptance criteria**:
+- [ ] Two widgets on the same page with different `data-primary-color` render with their own respective colors
+- [ ] Re-initialising a widget (hot reload / SPA navigation) does not accumulate `<style>` elements in `document.head`
+- [ ] No regression on single-instance deploys (dominant case today)
+- [ ] Visual smoke test in Moodle host page
+
+---
+
+### DEBT-023: Hoist `_resolve_request_id` audit-fallback helper into `vektra_shared`
+
+**Status**: planned | **Priority**: low | **Created**: 2026-04-27
+**Origin**: CodeRabbit review on PR #73 (v0.5.0 hardening), nitpick on `vektra-learn/src/vektra_learn/api.py:60-76`
+
+**Context**: DEBT-020 introduced a `_resolve_request_id(request) -> UUID` helper that synthesizes `uuid4()` when `request.state.request_id` is missing and emits a structlog warning. The helper is duplicated almost verbatim across `vektra-admin/src/vektra_admin/api.py`, `vektra-learn/src/vektra_learn/api.py`, and `vektra-ingest/src/vektra_ingest/api.py`. Logger usage is also subtly inconsistent: admin/ingest call `log.warning(...)` against a module-level `log`, while learn calls `structlog.get_logger(__name__).warning(...)` inline.
+
+Three near-duplicates is the threshold where extraction starts to pay off (a fourth caller is plausible if the platform grows new audited endpoints; behavioural drift between modules is the real risk).
+
+**Proposed approach**:
+1. Add `vektra_shared.audit.resolve_request_id(request: Request) -> UUID` (or a new `vektra_shared.request_id` module if `audit.py` should stay narrow).
+2. Standardize the logger call shape so all three modules emit the same `request_id_middleware_missing_fallback` event with identical keys.
+3. Replace the three local helpers with imports.
+4. Verify import-linter contracts still pass (`vektra_shared` is the only module the components are allowed to import from, so this is well within the existing contract).
+
+**Acceptance criteria**:
+- [ ] `_resolve_request_id` removed from `vektra-admin/api.py`, `vektra-learn/api.py`, `vektra-ingest/api.py`
+- [ ] Single shared helper in `vektra_shared` with the same signature and behaviour
+- [ ] Same structlog event name and keys regardless of caller
+- [ ] All existing audit-fallback tests still pass; helper unit-tested in `vektra-shared/tests`
+
+---
+
 ### INFRA-005: Docker log persistence across container restarts
 
 **Status**: planned | **Priority**: medium | **Created**: 2026-03-23
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1870e6e3..586d5e46 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -19,7 +19,7 @@ Convention (Keep a Changelog 1.1.0):
 
 <!-- Add entries under: Added, Changed, Deprecated, Removed, Fixed, Security -->
 
-## [0.5.0] - 2026-04-25
+## [0.5.0] - 2026-04-27
 
 Widget production-ready + instructor configuration.
 
@@ -41,6 +41,18 @@ Widget production-ready + instructor configuration.
 - **User-facing branding**: README, top-level docs h1s, and external surfaces now use **Vektra RAG** as the product name. Coordinated with [vektralabs/vektra-moodle#14](https://github.com/vektralabs/vektra-moodle/pull/14) which renames its README h1 to "Vektra RAG for Moodle". Repo name (`vektra-stack`), Python package names (`vektra_*`), Docker images, container names, CLI commands, and internal code identifiers are unchanged.
 - **widget footer label**: default "Powered by" link text changed from "Vektra" to "VektraLabs" — clearer maintainer-credit pattern (the link points to vektralabs.github.io, the org landing page) and avoids the residual short form. Integrators using the default branding will see the new label after upgrading the bundle; custom `data-powered-by-text` overrides are unaffected.
 - **widget styles**: button and accent colors now use `var(--vektra-primary, …)` so `data-primary-color` takes effect without rebuilding the bundle. Hover states use `filter: brightness()` so custom colors still feel interactive.
+- **widget primary-color scope (DEBT-018)**: the `--vektra-primary` override is now scoped to widget roots (`.vektra-chat-btn, .vektra-chat-panel`) instead of `:root`, so it no longer clobbers any unrelated `--vektra-primary` declarations on the host page. Repeated widget initialization reuses a single `<style id="vektra-primary-override">` node instead of accumulating duplicates (multi-instance / hot-reload safety).
+
+### Fixed
+
+- **audit log fallback (DEBT-020, NFR-007)**: sensitive admin, learn, and ingest endpoints now always write an audit row, even if the request-id middleware doesn't populate `request.state.request_id`. Each component declares a private `_resolve_request_id` helper that synthesizes a `uuid4()` fallback and emits a structlog warning so middleware misconfiguration is observable. Applied to `POST /api-keys`, `DELETE /api-keys/{id}`, `PATCH /admin/namespaces/{id}/config`, `GET /admin/conversations/{id}/turns`, `GET /api/v1/learn/conversations/{id}/turns`, and the vektra-ingest async + direct audit writers (used by `POST /api/v1/ingest`, batch ingest, deletion). Previous code skipped the audit silently when `request_id` was missing.
+- **test fakes**: renamed `self_inner` to `self` in nested `_FakeResult` / `_FakeSession` helpers inside `test_fetch_document_names_marks_archived` (style consistency with PEP 8; no behaviour change).
+
+### Security
+
+- **deps**: bumped `litellm` from `>=1.40,<1.82.7` to `>=1.83.10,<1.83.11` — closes 2 critical CVEs (authentication bypass via OIDC userinfo cache key collision) and several high-severity findings (authenticated command execution via MCP stdio test endpoints, SSTI in `/prompts/test`).
+- **deps-dev**: bumped `pytest` from `>=8.0` to `>=9.0.3` (full test suite green on the new major version).
+- **deps-dev**: bumped widget `esbuild` from `^0.24` to `^0.25`.
 
 ## [0.4.0] - 2026-04-11
 
diff --git a/pyproject.toml b/pyproject.toml
index 5db02b43..f369699a 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -13,7 +13,7 @@ dev = [
     "alembic>=1.13",
     "pyyaml>=6.0",
     "testcontainers[postgres]>=4.8",
-    "pytest>=8.0",
+    "pytest>=9.0.3",
     "pytest-asyncio>=0.24",
     "pytest-cov>=5.0",
     "ruff>=0.15",
diff --git a/uv.lock b/uv.lock
index 2ce11368..292b5847 100644
--- a/uv.lock
+++ b/uv.lock
@@ -3,16 +3,25 @@ revision = 3
 requires-python = ">=3.12"
 resolution-markers = [
     "python_full_version >= '3.14' and sys_platform == 'win32'",
-    "python_full_version >= '3.14' and sys_platform == 'emscripten'",
-    "python_full_version >= '3.14' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
-    "python_full_version >= '3.14' and sys_platform == 'darwin'",
+    "python_full_version >= '3.14' and platform_machine != 's390x' and sys_platform == 'emscripten'",
+    "python_full_version >= '3.14' and platform_machine == 's390x' and sys_platform == 'emscripten'",
+    "python_full_version >= '3.14' and platform_machine != 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version >= '3.14' and platform_machine == 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version >= '3.14' and platform_machine != 's390x' and sys_platform == 'darwin'",
+    "python_full_version >= '3.14' and platform_machine == 's390x' and sys_platform == 'darwin'",
     "python_full_version == '3.13.*' and sys_platform == 'win32'",
-    "python_full_version == '3.13.*' and sys_platform == 'emscripten'",
-    "python_full_version == '3.13.*' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
-    "python_full_version < '3.13' and sys_platform != 'darwin' and sys_platform != 'win32'",
-    "python_full_version < '3.13' and sys_platform == 'win32'",
-    "python_full_version == '3.13.*' and sys_platform == 'darwin'",
-    "python_full_version < '3.13' and sys_platform == 'darwin'",
+    "python_full_version == '3.13.*' and platform_machine != 's390x' and sys_platform == 'emscripten'",
+    "python_full_version == '3.13.*' and platform_machine == 's390x' and sys_platform == 'emscripten'",
+    "python_full_version == '3.13.*' and platform_machine != 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version == '3.13.*' and platform_machine == 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version < '3.13' and platform_machine != 's390x' and sys_platform != 'darwin' and sys_platform != 'win32'",
+    "python_full_version < '3.13' and platform_machine == 's390x' and sys_platform != 'darwin' and sys_platform != 'win32'",
+    "python_full_version < '3.13' and platform_machine != 's390x' and sys_platform == 'win32'",
+    "python_full_version < '3.13' and platform_machine == 's390x' and sys_platform == 'win32'",
+    "python_full_version == '3.13.*' and platform_machine != 's390x' and sys_platform == 'darwin'",
+    "python_full_version == '3.13.*' and platform_machine == 's390x' and sys_platform == 'darwin'",
+    "python_full_version < '3.13' and platform_machine != 's390x' and sys_platform == 'darwin'",
+    "python_full_version < '3.13' and platform_machine == 's390x' and sys_platform == 'darwin'",
 ]
 
 [manifest]
@@ -32,7 +41,7 @@ dev = [
     { name = "alembic", specifier = ">=1.13" },
     { name = "import-linter", specifier = ">=2.7" },
     { name = "mypy", specifier = ">=1.13" },
-    { name = "pytest", specifier = ">=8.0" },
+    { name = "pytest", specifier = ">=9.0.3" },
     { name = "pytest-asyncio", specifier = ">=0.24" },
     { name = "pytest-cov", specifier = ">=5.0" },
     { name = "pyyaml", specifier = ">=6.0" },
@@ -51,8 +60,8 @@ dependencies = [
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     { name = "pyyaml", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
     { name = "safetensors", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
-    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform == 'darwin'" },
-    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
+    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (platform_machine == 's390x' and sys_platform == 'darwin') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
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@@ -513,14 +522,14 @@ wheels = [
 
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+version = "8.1.8"
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 [[package]]
@@ -706,55 +715,55 @@ wheels = [
 
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-sdist = { url = "https://files.pythonhosted.org/packages/c9/74/b3ff8e6c8446842c3f5c837e9c3dfcfe2018ea6ecef224c710c85ef728f4/requests-2.32.5.tar.gz", hash = "sha256:dbba0bac56e100853db0ea71b82b4dfd5fe2bf6d3754a8893c3af500cec7d7cf", size = 134517, upload-time = "2025-08-18T20:46:02.573Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/34/64/8860370b167a9721e8956ae116825caff829224fbca0ca6e7bf8ddef8430/requests-2.33.0.tar.gz", hash = "sha256:c7ebc5e8b0f21837386ad0e1c8fe8b829fa5f544d8df3b2253bff14ef29d7652", size = 134232, upload-time = "2026-03-25T15:10:41.586Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/1e/db/4254e3eabe8020b458f1a747140d32277ec7a271daf1d235b70dc0b4e6e3/requests-2.32.5-py3-none-any.whl", hash = "sha256:2462f94637a34fd532264295e186976db0f5d453d1cdd31473c85a6a161affb6", size = 64738, upload-time = "2025-08-18T20:46:00.542Z" },
+    { url = "https://files.pythonhosted.org/packages/56/5d/c814546c2333ceea4ba42262d8c4d55763003e767fa169adc693bd524478/requests-2.33.0-py3-none-any.whl", hash = "sha256:3324635456fa185245e24865e810cecec7b4caf933d7eb133dcde67d48cee69b", size = 65017, upload-time = "2026-03-25T15:10:40.382Z" },
 ]
 
 [[package]]
@@ -4132,8 +4149,8 @@ dependencies = [
     { name = "numpy" },
     { name = "scikit-learn" },
     { name = "scipy" },
-    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform == 'darwin'" },
-    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform != 'darwin'" },
+    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
     { name = "tqdm" },
     { name = "transformers" },
     { name = "typing-extensions" },
@@ -4529,8 +4546,8 @@ dependencies = [
     { name = "huggingface-hub", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
     { name = "pyyaml", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
     { name = "safetensors", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
-    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform == 'darwin'" },
-    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
+    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (platform_machine == 's390x' and sys_platform == 'darwin') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
     { name = "torchvision", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/d7/2c/593109822fe735e637382aca6640c1102c19797f7791f1fd1dab2d6c3cb1/timm-1.0.25.tar.gz", hash = "sha256:47f59fc2754725735cc81bb83bcbfce5bec4ebd5d4bb9e69da57daa92fcfa768", size = 2414743, upload-time = "2026-02-23T16:49:00.137Z" }
@@ -4584,18 +4601,18 @@ name = "torch"
 version = "2.10.0"
 source = { registry = "https://download.pytorch.org/whl/cpu" }
 resolution-markers = [
-    "python_full_version >= '3.14' and sys_platform == 'darwin'",
-    "python_full_version == '3.13.*' and sys_platform == 'darwin'",
-    "python_full_version < '3.13' and sys_platform == 'darwin'",
+    "python_full_version >= '3.14' and platform_machine != 's390x' and sys_platform == 'darwin'",
+    "python_full_version == '3.13.*' and platform_machine != 's390x' and sys_platform == 'darwin'",
+    "python_full_version < '3.13' and platform_machine != 's390x' and sys_platform == 'darwin'",
 ]
 dependencies = [
-    { name = "filelock", marker = "sys_platform == 'darwin'" },
-    { name = "fsspec", marker = "sys_platform == 'darwin'" },
-    { name = "jinja2", marker = "sys_platform == 'darwin'" },
-    { name = "networkx", marker = "sys_platform == 'darwin'" },
-    { name = "setuptools", marker = "sys_platform == 'darwin'" },
-    { name = "sympy", marker = "sys_platform == 'darwin'" },
-    { name = "typing-extensions", marker = "sys_platform == 'darwin'" },
+    { name = "filelock", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "fsspec", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "jinja2", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "networkx", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "setuptools", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "sympy", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "typing-extensions", marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
 ]
 wheels = [
     { url = "https://download-r2.pytorch.org/whl/cpu/torch-2.10.0-1-cp312-none-macosx_11_0_arm64.whl", hash = "sha256:7fbbf409143a4fe0812a40c0b46a436030a7e1d14fe8c5234dfbe44df47f617e", upload-time = "2026-02-06T16:27:14Z" },
@@ -4615,22 +4632,31 @@ version = "2.10.0+cpu"
 source = { registry = "https://download.pytorch.org/whl/cpu" }
 resolution-markers = [
     "python_full_version >= '3.14' and sys_platform == 'win32'",
-    "python_full_version >= '3.14' and sys_platform == 'emscripten'",
-    "python_full_version >= '3.14' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version >= '3.14' and platform_machine != 's390x' and sys_platform == 'emscripten'",
+    "python_full_version >= '3.14' and platform_machine == 's390x' and sys_platform == 'emscripten'",
+    "python_full_version >= '3.14' and platform_machine != 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version >= '3.14' and platform_machine == 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version >= '3.14' and platform_machine == 's390x' and sys_platform == 'darwin'",
     "python_full_version == '3.13.*' and sys_platform == 'win32'",
-    "python_full_version == '3.13.*' and sys_platform == 'emscripten'",
-    "python_full_version == '3.13.*' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
-    "python_full_version < '3.13' and sys_platform != 'darwin' and sys_platform != 'win32'",
-    "python_full_version < '3.13' and sys_platform == 'win32'",
+    "python_full_version == '3.13.*' and platform_machine != 's390x' and sys_platform == 'emscripten'",
+    "python_full_version == '3.13.*' and platform_machine == 's390x' and sys_platform == 'emscripten'",
+    "python_full_version == '3.13.*' and platform_machine != 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version == '3.13.*' and platform_machine == 's390x' and sys_platform != 'darwin' and sys_platform != 'emscripten' and sys_platform != 'win32'",
+    "python_full_version < '3.13' and platform_machine != 's390x' and sys_platform != 'darwin' and sys_platform != 'win32'",
+    "python_full_version < '3.13' and platform_machine == 's390x' and sys_platform != 'darwin' and sys_platform != 'win32'",
+    "python_full_version < '3.13' and platform_machine != 's390x' and sys_platform == 'win32'",
+    "python_full_version < '3.13' and platform_machine == 's390x' and sys_platform == 'win32'",
+    "python_full_version == '3.13.*' and platform_machine == 's390x' and sys_platform == 'darwin'",
+    "python_full_version < '3.13' and platform_machine == 's390x' and sys_platform == 'darwin'",
 ]
 dependencies = [
-    { name = "filelock", marker = "sys_platform != 'darwin'" },
-    { name = "fsspec", marker = "sys_platform != 'darwin'" },
-    { name = "jinja2", marker = "sys_platform != 'darwin'" },
-    { name = "networkx", marker = "sys_platform != 'darwin'" },
-    { name = "setuptools", marker = "sys_platform != 'darwin'" },
-    { name = "sympy", marker = "sys_platform != 'darwin'" },
-    { name = "typing-extensions", marker = "sys_platform != 'darwin'" },
+    { name = "filelock", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
+    { name = "fsspec", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
+    { name = "jinja2", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
+    { name = "networkx", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
+    { name = "setuptools", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
+    { name = "sympy", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
+    { name = "typing-extensions", marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
 ]
 wheels = [
     { url = "https://download-r2.pytorch.org/whl/cpu/torch-2.10.0%2Bcpu-cp312-cp312-linux_aarch64.whl", hash = "sha256:8de5a36371b775e2d4881ed12cc7f2de400b1ad3d728aa74a281f649f87c9b8c", upload-time = "2026-01-23T15:10:22Z" },
@@ -4669,8 +4695,8 @@ source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "numpy", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
     { name = "pillow", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
-    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform == 'darwin'" },
-    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
+    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (platform_machine == 's390x' and sys_platform == 'darwin') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
 ]
 wheels = [
     { url = "https://files.pythonhosted.org/packages/56/3a/6ea0d73f49a9bef38a1b3a92e8dd455cea58470985d25635beab93841748/torchvision-0.25.0-cp312-cp312-macosx_11_0_arm64.whl", hash = "sha256:c2abe430c90b1d5e552680037d68da4eb80a5852ebb1c811b2b89d299b10573b", size = 1874920, upload-time = "2026-01-21T16:27:45.348Z" },
@@ -4729,7 +4755,7 @@ wheels = [
 
 [[package]]
 name = "typer"
-version = "0.24.0"
+version = "0.23.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "annotated-doc" },
@@ -4737,21 +4763,21 @@ dependencies = [
     { name = "rich" },
     { name = "shellingham" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/5a/b6/3e681d3b6bb22647509bdbfdd18055d5adc0dce5c5585359fa46ff805fdc/typer-0.24.0.tar.gz", hash = "sha256:f9373dc4eff901350694f519f783c29b6d7a110fc0dcc11b1d7e353b85ca6504", size = 118380, upload-time = "2026-02-16T22:08:48.496Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/fd/07/b822e1b307d40e263e8253d2384cf98c51aa2368cc7ba9a07e523a1d964b/typer-0.23.1.tar.gz", hash = "sha256:2070374e4d31c83e7b61362fd859aa683576432fd5b026b060ad6b4cd3b86134", size = 120047, upload-time = "2026-02-13T10:04:30.984Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/85/d0/4da85c2a45054bb661993c93524138ace4956cb075a7ae0c9d1deadc331b/typer-0.24.0-py3-none-any.whl", hash = "sha256:5fc435a9c8356f6160ed6e85a6301fdd6e3d8b2851da502050d1f92c5e9eddc8", size = 56441, upload-time = "2026-02-16T22:08:47.535Z" },
+    { url = "https://files.pythonhosted.org/packages/d5/91/9b286ab899c008c2cb05e8be99814807e7fbbd33f0c0c960470826e5ac82/typer-0.23.1-py3-none-any.whl", hash = "sha256:3291ad0d3c701cbf522012faccfbb29352ff16ad262db2139e6b01f15781f14e", size = 56813, upload-time = "2026-02-13T10:04:32.008Z" },
 ]
 
 [[package]]
 name = "typer-slim"
-version = "0.24.0"
+version = "0.23.1"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "typer" },
 ]
-sdist = { url = "https://files.pythonhosted.org/packages/a7/a7/e6aecc4b4eb59598829a3b5076a93aff291b4fdaa2ded25efc4e1f4d219c/typer_slim-0.24.0.tar.gz", hash = "sha256:f0ed36127183f52ae6ced2ecb2521789995992c521a46083bfcdbb652d22ad34", size = 4776, upload-time = "2026-02-16T22:08:51.2Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/da/22/b9c47b8655937b6877d40791b937931702ba9c5f9d28753199266aa96f50/typer_slim-0.23.1.tar.gz", hash = "sha256:dfe92a6317030ee2380f65bf92e540d7c77fefcc689e10d585b4925b45b5e06a", size = 4762, upload-time = "2026-02-13T10:04:26.416Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/a7/24/5480c20380dfd18cf33d14784096dca45a24eae6102e91d49a718d3b6855/typer_slim-0.24.0-py3-none-any.whl", hash = "sha256:d5d7ee1ee2834d5020c7c616ed5e0d0f29b9a4b1dd283bdebae198ec09778d0e", size = 3394, upload-time = "2026-02-16T22:08:49.92Z" },
+    { url = "https://files.pythonhosted.org/packages/ad/8a/5764b851659345f34787f1b6eb30b9d308bbd6c294825cbe38b6b869c97a/typer_slim-0.23.1-py3-none-any.whl", hash = "sha256:8146d5df1eb89f628191c4c604c8464fa841885d0733c58e6e700ff0228adac5", size = 3397, upload-time = "2026-02-13T10:04:27.132Z" },
 ]
 
 [[package]]
@@ -4866,8 +4892,8 @@ dependencies = [
     { name = "rapidfuzz", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
     { name = "scipy", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
     { name = "timm", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
-    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform == 'darwin'" },
-    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
+    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "(python_full_version < '3.13' and sys_platform == 'win32') or (platform_machine == 's390x' and sys_platform == 'darwin') or (sys_platform != 'darwin' and sys_platform != 'win32')" },
     { name = "transformers", marker = "python_full_version < '3.13' or sys_platform != 'win32'" },
 ]
 sdist = { url = "https://files.pythonhosted.org/packages/60/eb/7f19073948f50dacd2f4997b88207eb4ba12ad2ecb94e416b55849940564/unstructured_inference-1.5.2.tar.gz", hash = "sha256:5aa8e81009763fe44d17fc9305589ff5ffc168152d0edb73bc02978af49490bd", size = 46613, upload-time = "2026-02-13T01:01:38.702Z" }
@@ -5113,7 +5139,7 @@ dev = [
 requires-dist = [
     { name = "fastapi", specifier = ">=0.115" },
     { name = "jinja2", specifier = ">=3.1" },
-    { name = "litellm", specifier = ">=1.40,<1.82.7" },
+    { name = "litellm", specifier = ">=1.83.10" },
     { name = "presidio-analyzer", specifier = ">=2.2" },
     { name = "presidio-anonymizer", specifier = ">=2.2" },
     { name = "pydantic", specifier = ">=2,<3" },
@@ -5125,7 +5151,7 @@ requires-dist = [
 [package.metadata.requires-dev]
 dev = [
     { name = "httpx", specifier = ">=0.27" },
-    { name = "pytest", specifier = ">=8.0" },
+    { name = "pytest", specifier = ">=9.0.3" },
     { name = "pytest-asyncio", specifier = ">=1.0" },
 ]
 
@@ -5140,8 +5166,8 @@ dependencies = [
     { name = "pydantic" },
     { name = "sentence-transformers" },
     { name = "sqlalchemy", extra = ["asyncio"] },
-    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform == 'darwin'" },
-    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "sys_platform != 'darwin'" },
+    { name = "torch", version = "2.10.0", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine != 's390x' and sys_platform == 'darwin'" },
+    { name = "torch", version = "2.10.0+cpu", source = { registry = "https://download.pytorch.org/whl/cpu" }, marker = "platform_machine == 's390x' or sys_platform != 'darwin'" },
     { name = "vektra-shared" },
 ]
 
diff --git a/vektra-admin/src/vektra_admin/api.py b/vektra-admin/src/vektra_admin/api.py
index 64d7c6e2..aa7ae1b5 100644
--- a/vektra-admin/src/vektra_admin/api.py
+++ b/vektra-admin/src/vektra_admin/api.py
@@ -14,7 +14,7 @@
 
 from datetime import UTC, datetime
 from typing import Any
-from uuid import UUID
+from uuid import UUID, uuid4
 
 import structlog
 from fastapi import (
@@ -74,6 +74,22 @@
 
 log = structlog.get_logger(__name__)
 
+
+def _resolve_request_id(request: Request) -> UUID:
+    """Return ``request.state.request_id`` or synthesize a fallback ``uuid4()``.
+
+    Always returns a UUID so audit logging never silently skips sensitive
+    endpoints (NFR-007) when the request-id middleware misbehaves. Emits a
+    structlog warning on the fallback path so misconfiguration is observable.
+    """
+    rid: UUID | None = getattr(request.state, "request_id", None)
+    if rid is not None:
+        return rid
+    fallback = uuid4()
+    log.warning("request_id_middleware_missing_fallback", fallback=str(fallback))
+    return fallback
+
+
 router = APIRouter()
 _bearer = HTTPBearer(auto_error=False)
 
@@ -258,9 +274,10 @@ async def create_api_key(
     registry = getattr(request.app.state, "registry", None)
 
     key_info: ApiKeyInfo | None = None
+    is_bootstrap = _bootstrap.is_bootstrap_key(token)
 
     # --- Authenticate: bootstrap or admin key ---
-    if _bootstrap.is_bootstrap_key(token):
+    if is_bootstrap:
         # Check consumption before proceeding
         consumed = await _bootstrap.is_bootstrap_consumed(session)
         if consumed:
@@ -331,7 +348,7 @@ async def create_api_key(
     )
     session.add(new_key)
 
-    if _bootstrap.is_bootstrap_key(token):
+    if is_bootstrap:
         await _bootstrap.consume_bootstrap_key(session)
 
     await session.commit()
@@ -355,19 +372,17 @@ async def create_api_key(
     # NFR-007: log ALL authenticated requests, including bootstrap key usage.
     # AuditLogOrm.key_id is NOT a FK, so UUID(int=0) is safe as sentinel.
     _BOOTSTRAP_SENTINEL = UUID(int=0)
-    request_id = getattr(request.state, "request_id", None)
-    if request_id:
-        is_bootstrap = _bootstrap.is_bootstrap_key(token)
-        background_tasks.add_task(
-            _audit.log_event,
-            key_id=key_info.key_id if key_info else _BOOTSTRAP_SENTINEL,
-            endpoint="/api/v1/api-keys",
-            method="POST",
-            status_code=201,
-            request_id=request_id,
-            action="apikey_created_bootstrap" if is_bootstrap else "apikey_created",
-            log_metadata={"new_key_id": str(new_key.id)},
-        )
+    request_id = _resolve_request_id(request)
+    background_tasks.add_task(
+        _audit.log_event,
+        key_id=key_info.key_id if key_info else _BOOTSTRAP_SENTINEL,
+        endpoint="/api/v1/api-keys",
+        method="POST",
+        status_code=201,
+        request_id=request_id,
+        action="apikey_created_bootstrap" if is_bootstrap else "apikey_created",
+        log_metadata={"new_key_id": str(new_key.id)},
+    )
 
     log.info("api_key_created", key_id=str(new_key.id), scopes=requested_scopes)
 
@@ -449,18 +464,17 @@ async def revoke_api_key(
             pass
 
     # Audit log (async background task; log_event creates its own session)
-    request_id = getattr(request.state, "request_id", None)
-    if request_id:
-        background_tasks.add_task(
-            _audit.log_event,
-            key_id=key_info.key_id,
-            endpoint=f"/api/v1/api-keys/{key_id}",
-            method="DELETE",
-            status_code=204,
-            request_id=request_id,
-            action="apikey_revoked",
-            log_metadata={"revoked_key_id": str(key_id)},
-        )
+    request_id = _resolve_request_id(request)
+    background_tasks.add_task(
+        _audit.log_event,
+        key_id=key_info.key_id,
+        endpoint=f"/api/v1/api-keys/{key_id}",
+        method="DELETE",
+        status_code=204,
+        request_id=request_id,
+        action="apikey_revoked",
+        log_metadata={"revoked_key_id": str(key_id)},
+    )
 
     log.info("api_key_revoked", key_id=str(key_id), revoked_by=str(key_info.key_id))
 
@@ -519,22 +533,21 @@ async def get_conversation_turns(
         raise HTTPException(status_code=404, detail="Conversation not found")
 
     # Audit log: sensitive content access
-    request_id = getattr(request.state, "request_id", None)
-    if request_id:
-        background_tasks.add_task(
-            _audit.log_event,
-            key_id=_key.key_id,
-            endpoint=f"/api/v1/admin/conversations/{conversation_id}/turns",
-            method="GET",
-            status_code=200,
-            request_id=request_id,
-            action="conversation_turns_read",
-            log_metadata={
-                "namespace": getattr(request.state, "rls_namespace", None),
-                "conversation_id": str(conversation_id),
-                "turn_count": len(turns),
-            },
-        )
+    request_id = _resolve_request_id(request)
+    background_tasks.add_task(
+        _audit.log_event,
+        key_id=_key.key_id,
+        endpoint=f"/api/v1/admin/conversations/{conversation_id}/turns",
+        method="GET",
+        status_code=200,
+        request_id=request_id,
+        action="conversation_turns_read",
+        log_metadata={
+            "namespace": getattr(request.state, "rls_namespace", None),
+            "conversation_id": str(conversation_id),
+            "turn_count": len(turns),
+        },
+    )
 
     return turns
 
@@ -752,21 +765,20 @@ async def patch_namespace_config(
     await session.commit()
 
     # --- Audit log (NFR-007): config change is an administrative event ---
-    request_id = getattr(request.state, "request_id", None)
-    if request_id:
-        background_tasks.add_task(
-            _audit.log_event,
-            key_id=key_info.key_id,
-            endpoint=f"/api/v1/admin/namespaces/{namespace_id}/config",
-            method="PATCH",
-            status_code=200,
-            request_id=request_id,
-            action="namespace_config_updated",
-            log_metadata={
-                "namespace_id": namespace_id,
-                "updated_keys": sorted(body.keys()),
-            },
-        )
+    request_id = _resolve_request_id(request)
+    background_tasks.add_task(
+        _audit.log_event,
+        key_id=key_info.key_id,
+        endpoint=f"/api/v1/admin/namespaces/{namespace_id}/config",
+        method="PATCH",
+        status_code=200,
+        request_id=request_id,
+        action="namespace_config_updated",
+        log_metadata={
+            "namespace_id": namespace_id,
+            "updated_keys": sorted(body.keys()),
+        },
+    )
 
     log.info(
         "namespace_config_updated",
diff --git a/vektra-admin/tests/test_admin_turns.py b/vektra-admin/tests/test_admin_turns.py
index 97f4e54a..a87f7b6d 100644
--- a/vektra-admin/tests/test_admin_turns.py
+++ b/vektra-admin/tests/test_admin_turns.py
@@ -1,12 +1,13 @@
-"""Unit tests for admin conversation turns endpoint (DEBT-011)."""
+"""Unit tests for admin conversation turns endpoint (DEBT-011) and the
+shared request_id fallback helper (DEBT-020)."""
 
 from unittest.mock import AsyncMock, MagicMock
-from uuid import uuid4
+from uuid import UUID, uuid4
 
 import pytest
 from fastapi import HTTPException
 
-from vektra_admin.api import get_conversation_turns
+from vektra_admin.api import _resolve_request_id, get_conversation_turns
 
 
 @pytest.mark.asyncio
@@ -78,6 +79,74 @@ async def test_returns_404_when_conversation_not_found():
     assert exc_info.value.status_code == 404
 
 
+@pytest.mark.asyncio
+async def test_audits_with_synthetic_request_id_when_middleware_missing():
+    """Sensitive read endpoints must audit even if the request-id middleware
+    didn't populate ``request.state.request_id`` (NFR-007 / DEBT-020).
+    """
+    cid = uuid4()
+    turns = [
+        {
+            "turn_number": 1,
+            "question": "Q",
+            "answer": "A",
+            "response_id": uuid4(),
+            "model": "x",
+            "prompt_tokens": 1,
+            "completion_tokens": 1,
+            "created_at": "2026-03-28T10:00:00+00:00",
+        }
+    ]
+
+    conv_store = MagicMock()
+    conv_store.get_turns_detail = AsyncMock(return_value=turns)
+
+    registry = MagicMock()
+    registry.get = MagicMock(return_value=conv_store)
+
+    app_state = MagicMock()
+    app_state.registry = registry
+
+    request = MagicMock()
+    request.app.state = app_state
+    request.state.request_id = None  # middleware did not set it
+
+    background_tasks = MagicMock()
+    key_info = MagicMock()
+    key_info.scopes = ["admin"]
+
+    result = await get_conversation_turns(cid, request, background_tasks, key_info)
+    assert result == turns
+
+    # Audit must fire with a synthetic UUID request_id rather than skip.
+    background_tasks.add_task.assert_called_once()
+    call_kwargs = background_tasks.add_task.call_args.kwargs
+    assert call_kwargs["action"] == "conversation_turns_read"
+    assert isinstance(call_kwargs["request_id"], UUID)
+
+
+def test_resolve_request_id_returns_existing_when_present():
+    """Helper should pass through a UUID set by the middleware."""
+    rid = uuid4()
+    request = MagicMock()
+    request.state.request_id = rid
+    assert _resolve_request_id(request) == rid
+
+
+def test_resolve_request_id_synthesizes_uuid_when_missing():
+    """Helper should synthesize a fresh UUID per call when state attr missing."""
+    request = MagicMock()
+    request.state.request_id = None
+
+    result = _resolve_request_id(request)
+
+    assert isinstance(result, UUID)
+    # Two distinct calls produce distinct UUIDs (no shared state).
+    request2 = MagicMock()
+    request2.state.request_id = None
+    assert _resolve_request_id(request2) != result
+
+
 @pytest.mark.asyncio
 async def test_returns_501_for_inmemory_store():
     """Should raise 501 when conversation store has no get_turns_detail method."""
diff --git a/vektra-core/pyproject.toml b/vektra-core/pyproject.toml
index 55cc616f..9add4036 100644
--- a/vektra-core/pyproject.toml
+++ b/vektra-core/pyproject.toml
@@ -8,7 +8,7 @@ dependencies = [
     "vektra-shared",
     "fastapi>=0.115",
     "pydantic>=2,<3",
-    "litellm>=1.40,<1.82.7",
+    "litellm>=1.83.10",
     "jinja2>=3.1",
     "structlog>=24.0",
     "presidio-analyzer>=2.2",
@@ -33,7 +33,7 @@ vektra-shared = { workspace = true }
 
 [dependency-groups]
 dev = [
-    "pytest>=8.0",
+    "pytest>=9.0.3",
     "pytest-asyncio>=1.0",
     "httpx>=0.27",
 ]
diff --git a/vektra-core/tests/test_pipeline.py b/vektra-core/tests/test_pipeline.py
index 8e8c578b..ba03600c 100644
--- a/vektra-core/tests/test_pipeline.py
+++ b/vektra-core/tests/test_pipeline.py
@@ -473,17 +473,17 @@ async def test_fetch_document_names_marks_archived(monkeypatch):
     ]
 
     class _FakeResult:
-        def all(self_inner):
+        def all(self):
             return rows
 
     class _FakeSession:
-        async def __aenter__(self_inner):
-            return self_inner
+        async def __aenter__(self):
+            return self
 
-        async def __aexit__(self_inner, *_):
+        async def __aexit__(self, *_):
             return False
 
-        async def execute(self_inner, *_a, **_k):
+        async def execute(self, *_a, **_k):
             return _FakeResult()
 
     def _factory():
diff --git a/vektra-ingest/src/vektra_ingest/api.py b/vektra-ingest/src/vektra_ingest/api.py
index a4d078c6..32f17983 100644
--- a/vektra-ingest/src/vektra_ingest/api.py
+++ b/vektra-ingest/src/vektra_ingest/api.py
@@ -17,7 +17,7 @@
 
 from datetime import UTC, datetime
 from typing import Any
-from uuid import UUID
+from uuid import UUID, uuid4
 
 import structlog
 from fastapi import (
@@ -51,6 +51,22 @@
 
 log = structlog.get_logger(__name__)
 
+
+def _resolve_request_id(request: Request) -> UUID:
+    """Return ``request.state.request_id`` or synthesize a fallback ``uuid4()``.
+
+    Always returns a UUID so audit logging never silently skips sensitive
+    endpoints (NFR-007) when the request-id middleware misbehaves. Emits a
+    structlog warning on the fallback path so misconfiguration is observable.
+    """
+    rid: UUID | None = getattr(request.state, "request_id", None)
+    if rid is not None:
+        return rid
+    fallback = uuid4()
+    log.warning("request_id_middleware_missing_fallback", fallback=str(fallback))
+    return fallback
+
+
 router = APIRouter()
 
 # Sync/async file size threshold (REQ-029)
@@ -893,9 +909,7 @@ def _write_audit_log(
     """Fire-and-forget audit log write via background task."""
     from vektra_shared.audit import log_event
 
-    request_id = getattr(request.state, "request_id", None)
-    if request_id is None:
-        return
+    request_id = _resolve_request_id(request)
 
     background_tasks.add_task(
         log_event,
@@ -920,9 +934,7 @@ async def _write_audit_log_direct(
     """Write audit log directly (for error paths where BackgroundTasks don't run)."""
     from vektra_shared.audit import log_event
 
-    request_id = getattr(request.state, "request_id", None)
-    if request_id is None:
-        return
+    request_id = _resolve_request_id(request)
 
     try:
         await log_event(
diff --git a/vektra-learn/src/vektra_learn/api.py b/vektra-learn/src/vektra_learn/api.py
index ae925bc1..a5ee5ca9 100644
--- a/vektra-learn/src/vektra_learn/api.py
+++ b/vektra-learn/src/vektra_learn/api.py
@@ -57,6 +57,24 @@
 # Sentinel key_id for learn-originated conversations (JWT auth has no API key).
 _LEARN_SENTINEL_KEY_ID = UUID("00000000-0000-0000-0000-000000000000")
 
+
+def _resolve_request_id(request: Request) -> UUID:
+    """Return ``request.state.request_id`` or synthesize a fallback ``uuid4()``.
+
+    Always returns a UUID so audit logging never silently skips sensitive
+    endpoints (NFR-007) when the request-id middleware misbehaves. Emits a
+    structlog warning on the fallback path so misconfiguration is observable.
+    """
+    rid: UUID | None = getattr(request.state, "request_id", None)
+    if rid is not None:
+        return rid
+    fallback = uuid4()
+    structlog.get_logger(__name__).warning(
+        "request_id_middleware_missing_fallback", fallback=str(fallback)
+    )
+    return fallback
+
+
 router = APIRouter(prefix="/api/v1/learn", tags=["learn"])
 
 
@@ -623,7 +641,7 @@ async def get_conversation_turns(
     # unconditionally with a synthesized request_id if the middleware hasn't
     # set one — a missing correlation id must not silently skip the audit
     # row (compliance gap otherwise invisible).
-    request_id = getattr(request.state, "request_id", None) or uuid4()
+    request_id = _resolve_request_id(request)
     background_tasks.add_task(
         _audit_log_event,
         key_id=_LEARN_SENTINEL_KEY_ID,
diff --git a/vektra-learn/widget/package-lock.json b/vektra-learn/widget/package-lock.json
index 842d387f..6647b3c7 100644
--- a/vektra-learn/widget/package-lock.json
+++ b/vektra-learn/widget/package-lock.json
@@ -5,13 +5,13 @@
   "packages": {
     "": {
       "devDependencies": {
-        "esbuild": "^0.24"
+        "esbuild": "^0.25"
       }
     },
     "node_modules/@esbuild/aix-ppc64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/aix-ppc64/-/aix-ppc64-0.24.2.tgz",
-      "integrity": "sha512-thpVCb/rhxE/BnMLQ7GReQLLN8q9qbHmI55F4489/ByVg2aQaQ6kbcLb6FHkocZzQhxc4gx0sCk0tJkKBFzDhA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/aix-ppc64/-/aix-ppc64-0.25.0.tgz",
+      "integrity": "sha512-O7vun9Sf8DFjH2UtqK8Ku3LkquL9SZL8OLY1T5NZkA34+wG3OQF7cl4Ql8vdNzM6fzBbYfLaiRLIOZ+2FOCgBQ==",
       "cpu": [
         "ppc64"
       ],
@@ -26,9 +26,9 @@
       }
     },
     "node_modules/@esbuild/android-arm": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/android-arm/-/android-arm-0.24.2.tgz",
-      "integrity": "sha512-tmwl4hJkCfNHwFB3nBa8z1Uy3ypZpxqxfTQOcHX+xRByyYgunVbZ9MzUUfb0RxaHIMnbHagwAxuTL+tnNM+1/Q==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/android-arm/-/android-arm-0.25.0.tgz",
+      "integrity": "sha512-PTyWCYYiU0+1eJKmw21lWtC+d08JDZPQ5g+kFyxP0V+es6VPPSUhM6zk8iImp2jbV6GwjX4pap0JFbUQN65X1g==",
       "cpu": [
         "arm"
       ],
@@ -43,9 +43,9 @@
       }
     },
     "node_modules/@esbuild/android-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/android-arm64/-/android-arm64-0.24.2.tgz",
-      "integrity": "sha512-cNLgeqCqV8WxfcTIOeL4OAtSmL8JjcN6m09XIgro1Wi7cF4t/THaWEa7eL5CMoMBdjoHOTh/vwTO/o2TRXIyzg==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/android-arm64/-/android-arm64-0.25.0.tgz",
+      "integrity": "sha512-grvv8WncGjDSyUBjN9yHXNt+cq0snxXbDxy5pJtzMKGmmpPxeAmAhWxXI+01lU5rwZomDgD3kJwulEnhTRUd6g==",
       "cpu": [
         "arm64"
       ],
@@ -60,9 +60,9 @@
       }
     },
     "node_modules/@esbuild/android-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/android-x64/-/android-x64-0.24.2.tgz",
-      "integrity": "sha512-B6Q0YQDqMx9D7rvIcsXfmJfvUYLoP722bgfBlO5cGvNVb5V/+Y7nhBE3mHV9OpxBf4eAS2S68KZztiPaWq4XYw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/android-x64/-/android-x64-0.25.0.tgz",
+      "integrity": "sha512-m/ix7SfKG5buCnxasr52+LI78SQ+wgdENi9CqyCXwjVR2X4Jkz+BpC3le3AoBPYTC9NHklwngVXvbJ9/Akhrfg==",
       "cpu": [
         "x64"
       ],
@@ -77,9 +77,9 @@
       }
     },
     "node_modules/@esbuild/darwin-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/darwin-arm64/-/darwin-arm64-0.24.2.tgz",
-      "integrity": "sha512-kj3AnYWc+CekmZnS5IPu9D+HWtUI49hbnyqk0FLEJDbzCIQt7hg7ucF1SQAilhtYpIujfaHr6O0UHlzzSPdOeA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/darwin-arm64/-/darwin-arm64-0.25.0.tgz",
+      "integrity": "sha512-mVwdUb5SRkPayVadIOI78K7aAnPamoeFR2bT5nszFUZ9P8UpK4ratOdYbZZXYSqPKMHfS1wdHCJk1P1EZpRdvw==",
       "cpu": [
         "arm64"
       ],
@@ -94,9 +94,9 @@
       }
     },
     "node_modules/@esbuild/darwin-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/darwin-x64/-/darwin-x64-0.24.2.tgz",
-      "integrity": "sha512-WeSrmwwHaPkNR5H3yYfowhZcbriGqooyu3zI/3GGpF8AyUdsrrP0X6KumITGA9WOyiJavnGZUwPGvxvwfWPHIA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/darwin-x64/-/darwin-x64-0.25.0.tgz",
+      "integrity": "sha512-DgDaYsPWFTS4S3nWpFcMn/33ZZwAAeAFKNHNa1QN0rI4pUjgqf0f7ONmXf6d22tqTY+H9FNdgeaAa+YIFUn2Rg==",
       "cpu": [
         "x64"
       ],
@@ -111,9 +111,9 @@
       }
     },
     "node_modules/@esbuild/freebsd-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-arm64/-/freebsd-arm64-0.24.2.tgz",
-      "integrity": "sha512-UN8HXjtJ0k/Mj6a9+5u6+2eZ2ERD7Edt1Q9IZiB5UZAIdPnVKDoG7mdTVGhHJIeEml60JteamR3qhsr1r8gXvg==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-arm64/-/freebsd-arm64-0.25.0.tgz",
+      "integrity": "sha512-VN4ocxy6dxefN1MepBx/iD1dH5K8qNtNe227I0mnTRjry8tj5MRk4zprLEdG8WPyAPb93/e4pSgi1SoHdgOa4w==",
       "cpu": [
         "arm64"
       ],
@@ -128,9 +128,9 @@
       }
     },
     "node_modules/@esbuild/freebsd-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-x64/-/freebsd-x64-0.24.2.tgz",
-      "integrity": "sha512-TvW7wE/89PYW+IevEJXZ5sF6gJRDY/14hyIGFXdIucxCsbRmLUcjseQu1SyTko+2idmCw94TgyaEZi9HUSOe3Q==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/freebsd-x64/-/freebsd-x64-0.25.0.tgz",
+      "integrity": "sha512-mrSgt7lCh07FY+hDD1TxiTyIHyttn6vnjesnPoVDNmDfOmggTLXRv8Id5fNZey1gl/V2dyVK1VXXqVsQIiAk+A==",
       "cpu": [
         "x64"
       ],
@@ -145,9 +145,9 @@
       }
     },
     "node_modules/@esbuild/linux-arm": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm/-/linux-arm-0.24.2.tgz",
-      "integrity": "sha512-n0WRM/gWIdU29J57hJyUdIsk0WarGd6To0s+Y+LwvlC55wt+GT/OgkwoXCXvIue1i1sSNWblHEig00GBWiJgfA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm/-/linux-arm-0.25.0.tgz",
+      "integrity": "sha512-vkB3IYj2IDo3g9xX7HqhPYxVkNQe8qTK55fraQyTzTX/fxaDtXiEnavv9geOsonh2Fd2RMB+i5cbhu2zMNWJwg==",
       "cpu": [
         "arm"
       ],
@@ -162,9 +162,9 @@
       }
     },
     "node_modules/@esbuild/linux-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm64/-/linux-arm64-0.24.2.tgz",
-      "integrity": "sha512-7HnAD6074BW43YvvUmE/35Id9/NB7BeX5EoNkK9obndmZBUk8xmJJeU7DwmUeN7tkysslb2eSl6CTrYz6oEMQg==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-arm64/-/linux-arm64-0.25.0.tgz",
+      "integrity": "sha512-9QAQjTWNDM/Vk2bgBl17yWuZxZNQIF0OUUuPZRKoDtqF2k4EtYbpyiG5/Dk7nqeK6kIJWPYldkOcBqjXjrUlmg==",
       "cpu": [
         "arm64"
       ],
@@ -179,9 +179,9 @@
       }
     },
     "node_modules/@esbuild/linux-ia32": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-ia32/-/linux-ia32-0.24.2.tgz",
-      "integrity": "sha512-sfv0tGPQhcZOgTKO3oBE9xpHuUqguHvSo4jl+wjnKwFpapx+vUDcawbwPNuBIAYdRAvIDBfZVvXprIj3HA+Ugw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-ia32/-/linux-ia32-0.25.0.tgz",
+      "integrity": "sha512-43ET5bHbphBegyeqLb7I1eYn2P/JYGNmzzdidq/w0T8E2SsYL1U6un2NFROFRg1JZLTzdCoRomg8Rvf9M6W6Gg==",
       "cpu": [
         "ia32"
       ],
@@ -196,9 +196,9 @@
       }
     },
     "node_modules/@esbuild/linux-loong64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-loong64/-/linux-loong64-0.24.2.tgz",
-      "integrity": "sha512-CN9AZr8kEndGooS35ntToZLTQLHEjtVB5n7dl8ZcTZMonJ7CCfStrYhrzF97eAecqVbVJ7APOEe18RPI4KLhwQ==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-loong64/-/linux-loong64-0.25.0.tgz",
+      "integrity": "sha512-fC95c/xyNFueMhClxJmeRIj2yrSMdDfmqJnyOY4ZqsALkDrrKJfIg5NTMSzVBr5YW1jf+l7/cndBfP3MSDpoHw==",
       "cpu": [
         "loong64"
       ],
@@ -213,9 +213,9 @@
       }
     },
     "node_modules/@esbuild/linux-mips64el": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-mips64el/-/linux-mips64el-0.24.2.tgz",
-      "integrity": "sha512-iMkk7qr/wl3exJATwkISxI7kTcmHKE+BlymIAbHO8xanq/TjHaaVThFF6ipWzPHryoFsesNQJPE/3wFJw4+huw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-mips64el/-/linux-mips64el-0.25.0.tgz",
+      "integrity": "sha512-nkAMFju7KDW73T1DdH7glcyIptm95a7Le8irTQNO/qtkoyypZAnjchQgooFUDQhNAy4iu08N79W4T4pMBwhPwQ==",
       "cpu": [
         "mips64el"
       ],
@@ -230,9 +230,9 @@
       }
     },
     "node_modules/@esbuild/linux-ppc64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-ppc64/-/linux-ppc64-0.24.2.tgz",
-      "integrity": "sha512-shsVrgCZ57Vr2L8mm39kO5PPIb+843FStGt7sGGoqiiWYconSxwTiuswC1VJZLCjNiMLAMh34jg4VSEQb+iEbw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-ppc64/-/linux-ppc64-0.25.0.tgz",
+      "integrity": "sha512-NhyOejdhRGS8Iwv+KKR2zTq2PpysF9XqY+Zk77vQHqNbo/PwZCzB5/h7VGuREZm1fixhs4Q/qWRSi5zmAiO4Fw==",
       "cpu": [
         "ppc64"
       ],
@@ -247,9 +247,9 @@
       }
     },
     "node_modules/@esbuild/linux-riscv64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-riscv64/-/linux-riscv64-0.24.2.tgz",
-      "integrity": "sha512-4eSFWnU9Hhd68fW16GD0TINewo1L6dRrB+oLNNbYyMUAeOD2yCK5KXGK1GH4qD/kT+bTEXjsyTCiJGHPZ3eM9Q==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-riscv64/-/linux-riscv64-0.25.0.tgz",
+      "integrity": "sha512-5S/rbP5OY+GHLC5qXp1y/Mx//e92L1YDqkiBbO9TQOvuFXM+iDqUNG5XopAnXoRH3FjIUDkeGcY1cgNvnXp/kA==",
       "cpu": [
         "riscv64"
       ],
@@ -264,9 +264,9 @@
       }
     },
     "node_modules/@esbuild/linux-s390x": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-s390x/-/linux-s390x-0.24.2.tgz",
-      "integrity": "sha512-S0Bh0A53b0YHL2XEXC20bHLuGMOhFDO6GN4b3YjRLK//Ep3ql3erpNcPlEFed93hsQAjAQDNsvcK+hV90FubSw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-s390x/-/linux-s390x-0.25.0.tgz",
+      "integrity": "sha512-XM2BFsEBz0Fw37V0zU4CXfcfuACMrppsMFKdYY2WuTS3yi8O1nFOhil/xhKTmE1nPmVyvQJjJivgDT+xh8pXJA==",
       "cpu": [
         "s390x"
       ],
@@ -281,9 +281,9 @@
       }
     },
     "node_modules/@esbuild/linux-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/linux-x64/-/linux-x64-0.24.2.tgz",
-      "integrity": "sha512-8Qi4nQcCTbLnK9WoMjdC9NiTG6/E38RNICU6sUNqK0QFxCYgoARqVqxdFmWkdonVsvGqWhmm7MO0jyTqLqwj0Q==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/linux-x64/-/linux-x64-0.25.0.tgz",
+      "integrity": "sha512-9yl91rHw/cpwMCNytUDxwj2XjFpxML0y9HAOH9pNVQDpQrBxHy01Dx+vaMu0N1CKa/RzBD2hB4u//nfc+Sd3Cw==",
       "cpu": [
         "x64"
       ],
@@ -298,9 +298,9 @@
       }
     },
     "node_modules/@esbuild/netbsd-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/netbsd-arm64/-/netbsd-arm64-0.24.2.tgz",
-      "integrity": "sha512-wuLK/VztRRpMt9zyHSazyCVdCXlpHkKm34WUyinD2lzK07FAHTq0KQvZZlXikNWkDGoT6x3TD51jKQ7gMVpopw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/netbsd-arm64/-/netbsd-arm64-0.25.0.tgz",
+      "integrity": "sha512-RuG4PSMPFfrkH6UwCAqBzauBWTygTvb1nxWasEJooGSJ/NwRw7b2HOwyRTQIU97Hq37l3npXoZGYMy3b3xYvPw==",
       "cpu": [
         "arm64"
       ],
@@ -315,9 +315,9 @@
       }
     },
     "node_modules/@esbuild/netbsd-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/netbsd-x64/-/netbsd-x64-0.24.2.tgz",
-      "integrity": "sha512-VefFaQUc4FMmJuAxmIHgUmfNiLXY438XrL4GDNV1Y1H/RW3qow68xTwjZKfj/+Plp9NANmzbH5R40Meudu8mmw==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/netbsd-x64/-/netbsd-x64-0.25.0.tgz",
+      "integrity": "sha512-jl+qisSB5jk01N5f7sPCsBENCOlPiS/xptD5yxOx2oqQfyourJwIKLRA2yqWdifj3owQZCL2sn6o08dBzZGQzA==",
       "cpu": [
         "x64"
       ],
@@ -332,9 +332,9 @@
       }
     },
     "node_modules/@esbuild/openbsd-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/openbsd-arm64/-/openbsd-arm64-0.24.2.tgz",
-      "integrity": "sha512-YQbi46SBct6iKnszhSvdluqDmxCJA+Pu280Av9WICNwQmMxV7nLRHZfjQzwbPs3jeWnuAhE9Jy0NrnJ12Oz+0A==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/openbsd-arm64/-/openbsd-arm64-0.25.0.tgz",
+      "integrity": "sha512-21sUNbq2r84YE+SJDfaQRvdgznTD8Xc0oc3p3iW/a1EVWeNj/SdUCbm5U0itZPQYRuRTW20fPMWMpcrciH2EJw==",
       "cpu": [
         "arm64"
       ],
@@ -349,9 +349,9 @@
       }
     },
     "node_modules/@esbuild/openbsd-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/openbsd-x64/-/openbsd-x64-0.24.2.tgz",
-      "integrity": "sha512-+iDS6zpNM6EnJyWv0bMGLWSWeXGN/HTaF/LXHXHwejGsVi+ooqDfMCCTerNFxEkM3wYVcExkeGXNqshc9iMaOA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/openbsd-x64/-/openbsd-x64-0.25.0.tgz",
+      "integrity": "sha512-2gwwriSMPcCFRlPlKx3zLQhfN/2WjJ2NSlg5TKLQOJdV0mSxIcYNTMhk3H3ulL/cak+Xj0lY1Ym9ysDV1igceg==",
       "cpu": [
         "x64"
       ],
@@ -366,9 +366,9 @@
       }
     },
     "node_modules/@esbuild/sunos-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/sunos-x64/-/sunos-x64-0.24.2.tgz",
-      "integrity": "sha512-hTdsW27jcktEvpwNHJU4ZwWFGkz2zRJUz8pvddmXPtXDzVKTTINmlmga3ZzwcuMpUvLw7JkLy9QLKyGpD2Yxig==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/sunos-x64/-/sunos-x64-0.25.0.tgz",
+      "integrity": "sha512-bxI7ThgLzPrPz484/S9jLlvUAHYMzy6I0XiU1ZMeAEOBcS0VePBFxh1JjTQt3Xiat5b6Oh4x7UC7IwKQKIJRIg==",
       "cpu": [
         "x64"
       ],
@@ -383,9 +383,9 @@
       }
     },
     "node_modules/@esbuild/win32-arm64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/win32-arm64/-/win32-arm64-0.24.2.tgz",
-      "integrity": "sha512-LihEQ2BBKVFLOC9ZItT9iFprsE9tqjDjnbulhHoFxYQtQfai7qfluVODIYxt1PgdoyQkz23+01rzwNwYfutxUQ==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/win32-arm64/-/win32-arm64-0.25.0.tgz",
+      "integrity": "sha512-ZUAc2YK6JW89xTbXvftxdnYy3m4iHIkDtK3CLce8wg8M2L+YZhIvO1DKpxrd0Yr59AeNNkTiic9YLf6FTtXWMw==",
       "cpu": [
         "arm64"
       ],
@@ -400,9 +400,9 @@
       }
     },
     "node_modules/@esbuild/win32-ia32": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/win32-ia32/-/win32-ia32-0.24.2.tgz",
-      "integrity": "sha512-q+iGUwfs8tncmFC9pcnD5IvRHAzmbwQ3GPS5/ceCyHdjXubwQWI12MKWSNSMYLJMq23/IUCvJMS76PDqXe1fxA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/win32-ia32/-/win32-ia32-0.25.0.tgz",
+      "integrity": "sha512-eSNxISBu8XweVEWG31/JzjkIGbGIJN/TrRoiSVZwZ6pkC6VX4Im/WV2cz559/TXLcYbcrDN8JtKgd9DJVIo8GA==",
       "cpu": [
         "ia32"
       ],
@@ -417,9 +417,9 @@
       }
     },
     "node_modules/@esbuild/win32-x64": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/@esbuild/win32-x64/-/win32-x64-0.24.2.tgz",
-      "integrity": "sha512-7VTgWzgMGvup6aSqDPLiW5zHaxYJGTO4OokMjIlrCtf+VpEL+cXKtCvg723iguPYI5oaUNdS+/V7OU2gvXVWEg==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/@esbuild/win32-x64/-/win32-x64-0.25.0.tgz",
+      "integrity": "sha512-ZENoHJBxA20C2zFzh6AI4fT6RraMzjYw4xKWemRTRmRVtN9c5DcH9r/f2ihEkMjOW5eGgrwCslG/+Y/3bL+DHQ==",
       "cpu": [
         "x64"
       ],
@@ -434,9 +434,9 @@
       }
     },
     "node_modules/esbuild": {
-      "version": "0.24.2",
-      "resolved": "https://registry.npmjs.org/esbuild/-/esbuild-0.24.2.tgz",
-      "integrity": "sha512-+9egpBW8I3CD5XPe0n6BfT5fxLzxrlDzqydF3aviG+9ni1lDC/OvMHcxqEFV0+LANZG5R1bFMWfUrjVsdwxJvA==",
+      "version": "0.25.0",
+      "resolved": "https://registry.npmjs.org/esbuild/-/esbuild-0.25.0.tgz",
+      "integrity": "sha512-BXq5mqc8ltbaN34cDqWuYKyNhX8D/Z0J1xdtdQ8UcIIIyJyz+ZMKUt58tF3SrZ85jcfN/PZYhjR5uDQAYNVbuw==",
       "dev": true,
       "hasInstallScript": true,
       "license": "MIT",
@@ -447,31 +447,31 @@
         "node": ">=18"
       },
       "optionalDependencies": {
-        "@esbuild/aix-ppc64": "0.24.2",
-        "@esbuild/android-arm": "0.24.2",
-        "@esbuild/android-arm64": "0.24.2",
-        "@esbuild/android-x64": "0.24.2",
-        "@esbuild/darwin-arm64": "0.24.2",
-        "@esbuild/darwin-x64": "0.24.2",
-        "@esbuild/freebsd-arm64": "0.24.2",
-        "@esbuild/freebsd-x64": "0.24.2",
-        "@esbuild/linux-arm": "0.24.2",
-        "@esbuild/linux-arm64": "0.24.2",
-        "@esbuild/linux-ia32": "0.24.2",
-        "@esbuild/linux-loong64": "0.24.2",
-        "@esbuild/linux-mips64el": "0.24.2",
-        "@esbuild/linux-ppc64": "0.24.2",
-        "@esbuild/linux-riscv64": "0.24.2",
-        "@esbuild/linux-s390x": "0.24.2",
-        "@esbuild/linux-x64": "0.24.2",
-        "@esbuild/netbsd-arm64": "0.24.2",
-        "@esbuild/netbsd-x64": "0.24.2",
-        "@esbuild/openbsd-arm64": "0.24.2",
-        "@esbuild/openbsd-x64": "0.24.2",
-        "@esbuild/sunos-x64": "0.24.2",
-        "@esbuild/win32-arm64": "0.24.2",
-        "@esbuild/win32-ia32": "0.24.2",
-        "@esbuild/win32-x64": "0.24.2"
+        "@esbuild/aix-ppc64": "0.25.0",
+        "@esbuild/android-arm": "0.25.0",
+        "@esbuild/android-arm64": "0.25.0",
+        "@esbuild/android-x64": "0.25.0",
+        "@esbuild/darwin-arm64": "0.25.0",
+        "@esbuild/darwin-x64": "0.25.0",
+        "@esbuild/freebsd-arm64": "0.25.0",
+        "@esbuild/freebsd-x64": "0.25.0",
+        "@esbuild/linux-arm": "0.25.0",
+        "@esbuild/linux-arm64": "0.25.0",
+        "@esbuild/linux-ia32": "0.25.0",
+        "@esbuild/linux-loong64": "0.25.0",
+        "@esbuild/linux-mips64el": "0.25.0",
+        "@esbuild/linux-ppc64": "0.25.0",
+        "@esbuild/linux-riscv64": "0.25.0",
+        "@esbuild/linux-s390x": "0.25.0",
+        "@esbuild/linux-x64": "0.25.0",
+        "@esbuild/netbsd-arm64": "0.25.0",
+        "@esbuild/netbsd-x64": "0.25.0",
+        "@esbuild/openbsd-arm64": "0.25.0",
+        "@esbuild/openbsd-x64": "0.25.0",
+        "@esbuild/sunos-x64": "0.25.0",
+        "@esbuild/win32-arm64": "0.25.0",
+        "@esbuild/win32-ia32": "0.25.0",
+        "@esbuild/win32-x64": "0.25.0"
       }
     }
   }
diff --git a/vektra-learn/widget/package.json b/vektra-learn/widget/package.json
index a33e4caf..32421588 100644
--- a/vektra-learn/widget/package.json
+++ b/vektra-learn/widget/package.json
@@ -4,6 +4,6 @@
     "build": "node esbuild.config.mjs"
   },
   "devDependencies": {
-    "esbuild": "^0.24"
+    "esbuild": "^0.25"
   }
 }
diff --git a/vektra-learn/widget/src/chat-ui.js b/vektra-learn/widget/src/chat-ui.js
index d38a1f3b..f2291075 100644
--- a/vektra-learn/widget/src/chat-ui.js
+++ b/vektra-learn/widget/src/chat-ui.js
@@ -139,11 +139,18 @@ export class ChatUI {
     document.head.appendChild(style);
 
     if (this._primaryColor) {
-      const override = document.createElement("style");
-      // Single CSS custom property; styles.js uses var(--vektra-primary, ...)
-      // so an invalid value (filtered above) never reaches the DOM.
-      override.textContent = `:root { --vektra-primary: ${this._primaryColor}; }`;
-      document.head.appendChild(override);
+      // Reuse a single override node — only the primary-color override is
+      // deduped, not the main style block above (DEBT-018 scope: avoid the
+      // override leaking to host page :root and clobbering unrelated
+      // --vektra-primary uses; main-style accumulation across hot reloads is
+      // not tackled here, see DEBT-022 for multi-instance support).
+      let override = document.getElementById("vektra-primary-override");
+      if (!override) {
+        override = document.createElement("style");
+        override.id = "vektra-primary-override";
+        document.head.appendChild(override);
+      }
+      override.textContent = `.vektra-chat-btn, .vektra-chat-panel { --vektra-primary: ${this._primaryColor}; }`;
     }
   }