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## Thinking Path > - Paperclip is the open source app people use to manage AI agents for work. > - The server keeps attachments and other files in a storage provider. Hosted instances use the S3 provider. > - Sentry received `SignatureDoesNotMatch` errors from the S3 provider on two staging hosts. > - The events have only AWS SDK stack frames. They do not show which S3 call failed, the HTTP status, or the S3 request ID. > - Without these facts, we cannot find the cause or make a safe fix. > - This pull request records a small, fixed-shape failure record on the S3 error and sends it with the Sentry event. > - The benefit is that the next event shows the failed operation and the provider request ID, and no private data goes to Sentry. ## Linked Issues or Issue Description **What happened?** The S3 storage provider threw `SignatureDoesNotMatch` four times on staging. The Sentry events do not identify the S3 operation or the caller. **Expected behavior** A storage provider failure in Sentry shows which storage call failed and the provider's correlation fields. **Steps to reproduce** 1. Configure the S3 storage provider against an endpoint that rejects the request signature. 2. Read, write, check, or delete a stored file. 3. Look at the Sentry event. It has no first-party stack frame and no operation name. No public GitHub issue exists. I searched open and closed pull requests for `SignatureDoesNotMatch` and storage failure diagnostics. No pull request covers this. ## What Changed - Add `server/src/storage/failure-diagnostics.ts`. It keeps a frozen, fixed-shape record for each failed storage error in a `WeakMap`. - Add `server/src/storage/s3-failure.ts`. It wraps each S3 call and records the operation, error code, HTTP status, request ID, and SDK attempt count. It reads only data properties. A value that does not match its bounded format becomes `unknown` or `null`. - Wrap `PutObject`, `GetObject`, `HeadObject`, `DeleteObject`, `CreateMultipartUpload`, `UploadPart`, and `CompleteMultipartUpload`. - In `captureException`, add the `storage_operation` and `storage_error_code` tags and a `storage_failure` context to the event of that error only. The original error and its default grouping do not change. - Document the new context in `doc/observability.md`. ## Verification - `pnpm exec vitest run src/__tests__/storage-s3-failure-diagnostics.test.ts src/__tests__/sentry.test.ts` (in `server/`): 37 passed, 5 skipped. The skipped tests are the existing real-SDK tests, which need an environment flag. - `pnpm exec vitest run src/__tests__/storage-s3-multipart.test.ts src/__tests__/storage-local-provider.test.ts`: 8 passed. - The new tests use a local HTTP server that returns a real S3 `SignatureDoesNotMatch` XML body with a `StringToSign` field. The tests make sure that the record has the operation, code, status and request ID, and that it does not contain the private string. - I typechecked the changed source files with a scoped `tsc` project. They have no errors. I could not run the full `pnpm -r typecheck` and `pnpm build` in my sandbox: it has a 4 GiB memory limit and no `cargo` for the runner binary. CI runs the full checks. ## Risks - Low risk. The change adds a `try`/`catch` that records data and throws the same error again. Storage behavior, not-found handling, and HTTP responses do not change. - Secret-sensitive routes replace the error before reporting, so those events do not get the record. This is intended. - The record never contains the bucket, object key, endpoint, credentials, error message, or provider response body. ## Model Used - Claude Opus 5.5 (`claude-opus-5-5`), Anthropic. Used through Claude Code with tool use (shell, file edit) and extended reasoning. ## 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>