Files
PaperClipAI/server
Nicky LeachandPaperclip c276d3fdc3 feat(observability): report terminal run failures to Sentry (#13446)
## 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>
2026-09-14 23:32:15 -07:00
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