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## Thinking Path
> - Paperclip is the open source app people use to manage AI agents for
work.
> - The server sends a Sentry `run_failure` event when an agent run
reaches a terminal failure.
> - A native run that waits for a same-run retry is stored as `failed`
with `nativePhase: "retryable_failure"`. That state is not terminal.
> - `reportRunFailure` reported that pending state. Runs that later
recovered, for example after a workspace copy-back retry, still sent a
run failure event.
> - These events make one catch-all Sentry group noisy and hide the real
terminal failures in it.
> - This pull request skips the pending retry state and reports once
when the retry ends as a terminal failure.
> - The benefit is that run failure events match runs that really
failed.
## Linked Issues or Issue Description
**What happened?**
Two staging runs had a workspace copy-back failure during settlement
(`Daytona syncOut tar command failed ... No space left on device`). The
executor stored each run as `failed` with `nativePhase:
"retryable_failure"` and `errorCode: native_session_interrupted`. Sentry
received a `run_failure` event for each run. About two minutes later,
the copy-back retry succeeded and both runs finished as `succeeded` with
`workspaceFinalizeStatus: "succeeded"`.
**Expected behavior**
A run that waits for a same-run retry must not send a terminal run
failure event. If the retry ends as a terminal failure, the server must
send one event at that time.
**Steps to reproduce**
1. Set `PAPERCLIP_SENTRY_RUN_FAILURES=unexpected`.
2. Start a native run that fails retryably. For example, make the
workspace copy-back fail once.
3. See the `run_failure` event in Sentry, and then see the run finish as
`succeeded` after the retry.
## What Changed
- `reportRunFailure` returns without a report for a native run that is
`failed` with `nativePhase: "retryable_failure"`.
- New `isNewTerminalRunFailure(before, after)`: a status change counts
as before. A failed run that leaves the pending retry state but stays
`failed` also counts.
- Three terminal writers can keep the status `failed` → `failed`. They
now use `isNewTerminalRunFailure`, so they still report once:
- the resume reconciler's ambiguous-state write;
- the restart recovery `blocked` write;
- the committed-result projection (`projectCommittedRun`).
- Result-less retries already reset the run to `running` before they
start, so their terminal write still reports through the existing
status-change guard.
- `doc/observability.md` describes the new rule.
## Verification
- `pnpm exec vitest run
src/services/__tests__/run-failure-report.test.ts
src/__tests__/run-failure-sentry.test.ts
src/__tests__/native-session-resumption.test.ts
src/services/native-runtime/native-run-finalizer-telemetry.test.ts
src/services/native-runtime/native-runner-restart-recovery.integration.test.ts
src/__tests__/heartbeat-status-preserving-telemetry.test.ts
src/services/execution-control-reconciliation.test.ts` (from `server/`):
7 files, 363 passed, 9 skipped.
- New tests:
- `run-failure-report.test.ts`: a pending native retry does not report,
and a `terminal_failure` run does. Unit cases cover
`isNewTerminalRunFailure`.
- `native-session-resumption.test.ts`: a sweep that ends an unreported
pending retry sends one event.
- `native-run-finalizer-telemetry.test.ts`: a committed failure for a
pending-retry row sends one event, and a replay sends none.
- `native-runner-restart-recovery.integration.test.ts`: a restart
recovery `blocked` write for a pending-retry row sends one event.
- I removed each of the three writer changes one at a time. The matching
new test failed each time (`expected [] to have a length of 1` / `to
deeply equal [ [ ObjectContaining{…} ] ]`).
- I did not run the full server `tsc --noEmit` locally. The local
container has a 4 GiB memory limit, and the process was killed (exit
137). CI runs the typecheck.
## Risks
- A run that stays in the pending retry state and never resumes no
longer sends a run failure event. The run stays visible on the board as
failed with a scheduled retry. A later terminal write still reports it.
- The finalizer's `failed` + `retryable_failure` write for a failed
provider result also stops reporting. The terminal write that ends that
retry reports instead: retry exhaustion in `recordRetryableFailure`
reports unconditionally, and commit goes through `finalizeNativeRun` or
`projectCommittedRun`.
- A run that was reported in the pending state before this change can
report once more when it becomes terminal after deploy. This affects
only runs in flight during the upgrade.
- There are no schema, migration, or API changes. Run status, retries,
and recovery do not change.
> For core feature work, check [`ROADMAP.md`](ROADMAP.md) first and
discuss it in `#dev` before opening the PR. Feature PRs that overlap
with planned core work may need to be redirected — check the roadmap
first. See `CONTRIBUTING.md`.
## Model Used
- Anthropic Claude Opus 5.5 (`claude-opus-5-5`) in Claude Code, with
tool use (shell, code search, test runs) and a read-only code
exploration subagent. Context window: the standard window for that
model.
## 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
- [ ] All Paperclip CI gates are green
- [ ] Greptile is 5/5 with no open P2s, recommendations, or follow-ups
- [x] I will address all Greptile and reviewer comments before
requesting merge
🤖 Generated with [Claude Code](https://claude.com/claude-code)
Co-authored-by: devinfoley <139239+devinfoley@users.noreply.github.com>
Co-authored-by: Claude Opus 5.5 <noreply@anthropic.com>