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## Thinking Path > - Paperclip manages work for AI agents and their companies. > - Cloud instances proxy a trusted user's portfolio through the control plane. > - A failed request returns a generic error to the client. > - That replacement error loses the failure phase and network code in Sentry. > - Operators need bounded evidence without upstream messages or credentials. > - This PR adds safe diagnostics while preserving the existing request behavior. ## Linked Issues or Issue Description Refs #10850, which added the portfolio proxy. No open PR for this diagnostic gap was found. **What happened?** A rejected portfolio fetch becomes a generic 502 in Sentry. The event cannot distinguish a connection reset, deadline, HTTP response failure, or body failure. The route's previous warning also included the original error and a stack identifier. **Steps to reproduce** Make the portfolio proxy's fetch reject with a TypeError whose cause has `code: ECONNRESET`. The client correctly receives the generic 502, but the captured replacement error loses that code. **Expected behavior** Keep the existing client response. Attach only bounded server-side diagnostic fields to the failure event. Do not retry the request or expose the original error. ## What Changed - Add a typed portfolio error with a private frozen diagnostic record: phase, upstream HTTP status, elapsed milliseconds, and an allowlisted network code. - Read at most four error/cause objects through own data properties. Unknown codes, messages, getters, and out-of-range values do not enter the record. - Replace the route's raw-error warnings with safe fields. Send a plain error plus event-local context through the existing optional Sentry gate. Keep the route callsite and default fingerprint policy. - Preserve authentication, trusted headers, cookies, exact HTTP error bodies, cache behavior, the ten-second deadline, and one fetch per request. Public responses receive no diagnostic fields. - Document the fields and test HTTP behavior, privacy, and event isolation with the real Sentry SDK. ## Verification - `PAPERCLIP_REQUIRE_SENTRY_TEST_SDK=1 pnpm exec vitest run server/src/__tests__/cloud-portfolio-error.test.ts server/src/__tests__/cloud-routes.test.ts server/src/__tests__/sentry.test.ts server/src/__tests__/run-failure-sentry-real-sdk.test.ts`: 65 passed, with the audited optional SDK installed. - Full local `pnpm -r typecheck` and `pnpm build` passed on Node 24.21.0 and pnpm 9.15.4. - Independent review found no blockers and independently passed all 65 tests, including the real SDK checks, on this exact commit. - Full Linux CI passed on this exact commit and provides aggregate suite coverage (54 successful checks, 2 intentional skips). A duplicate full local aggregate was not run. - The first SDK contract job failed before tests when npm could not resolve an OpenTelemetry transitive package. A subsequent empty-cache install first encountered a missing tarball, then succeeded after the registry artifact became available. All 6 real-SDK tests passed against that fresh install; the single unchanged-head CI retry passed. The SDK pin, workflow, and dependency files are unchanged. - The first browser shard 8 run timed out waiting for the inbox retry reply after 45 seconds. The unchanged isolated case passed (1/1), and the test, UI handler, fixture, and recovery files match the base commit. The failed log contains no wakeup POST before the test's immediate navigation; a navigation/request timing race is suspected but unproven without a trace. The single unchanged-head shard retry passed (20 passed, 1 skipped); no timeout or source change was made. - Greptile reviewed this exact commit at 5/5 with no unresolved review threads. - No live portfolio request was replayed. Route tests use controlled local upstream responses. - The added diff passed the secret and PII scan and `git diff --check`. ## Risks This is a diagnostic change. It does not identify or repair the origin of a connection reset. Unknown transport failures remain `unknown`. Elapsed values outside 0–60,000 ms become null. Default Sentry fingerprinting remains enabled; exact historical group membership is not guaranteed. No retry, migration, deployment, or configuration change is included. ## Model Used OpenAI GPT-6 through Codex, with reasoning, repository editing, code execution, and independent agent review. The exact deployment model ID and context window are not exposed in this session. ## Checklist - [x] I have included a thinking path that traces from project context to this change - [x] I have specified the model used (with version and capability details) - [x] I have checked ROADMAP.md and confirmed this PR does not duplicate planned core work - [x] I have searched GitHub for duplicate or related PRs and linked them above - [x] I have either (a) linked existing issues with `Fixes: #` / `Closes #` / `Refs #` OR (b) described the issue in-PR following the relevant issue template - [x] I have not referenced internal/instance-local Paperclip issues or links (only public GitHub `#NNN` / `github.com/paperclipai/paperclip` URLs) - [x] My branch name describes the change (e.g. `docs/...`, `fix/...`) and contains no internal Paperclip ticket id or instance-derived details - [x] I have run tests locally and they pass - [x] I have added or updated tests where applicable - [x] I have updated relevant documentation to reflect my changes - [x] I have considered and documented any risks above - [x] All Paperclip CI gates are green - [x] Greptile is 5/5 with no open P2s, recommendations, or follow-ups - [x] I will address all Greptile and reviewer comments before requesting merge Co-authored-by: Paperclip <noreply@paperclip.ing>