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## Thinking Path > - Paperclip is the open source app people use to manage AI agents for work. > - The server records the state of each agent run. > - Terminal run failures need clear error tracking for operators. > - The server did not report terminal `failed` or `timed_out` transitions to Sentry. > - This pull request reports each genuine terminal failure transition with safe diagnostic data. > - The benefit is faster diagnosis without changing run control flow or exposing credentials. ## Linked Issues or Issue Description **What happened?** The server wrote terminal run failures but did not report them to Sentry. Operators could not see these failures in error tracking. **Expected behavior** The server should report each genuine transition to `failed` or `timed_out` to Sentry. **Steps to reproduce** 1. Run an agent task that reaches a terminal failure state. 2. Inspect the Sentry events for the server. 3. Observe that the terminal run failure has no matching Sentry event. **Paperclip version or commit** The change targets the current `master` branch. No public GitHub issue or pull request covers this change. ## What Changed - Add `captureRunFailure()` as a fail-open Sentry entry point. - Add `reportRunFailure()` to filter status, resolve the adapter, redact text, and report the failure. - Call `reportRunFailure()` beside each of the eight terminal status writers. - Report six diagnostic values: the instance host, task identifier, run identifier, error message, error code, and agent adapter. - Group events by error code and agent adapter while keeping the redacted message in the event. - Report only genuine transitions and avoid duplicate finalization events. - Keep Sentry failures outside run control flow. ## Verification - `pnpm vitest run server/src/services/__tests__/run-failure-report.test.ts server/src/__tests__/run-failure-sentry.test.ts server/src/__tests__/native-session-resumption.test.ts` - `pnpm vitest run server/src/services/execution-control-reconciliation.test.ts` - `pnpm --filter @paperclipai/server typecheck` - The full continuous-integration suite must run on this pull request. ## Risks - The report path can add diagnostic events when Sentry is configured. - The report path returns without action when Sentry is not configured. - Redaction runs before length limits and before the event leaves the process. - The change has no migration and no schema change. ## Model Used OpenAI Codex, GPT-5, tool use and code review support. The exact context window and reasoning configuration are not exposed by the runtime. ## 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>