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## Thinking Path > - Paperclip is the open source app people use to manage AI agents for work > - Operators delete a sandbox environment, optionally with consent to destroy its sandboxes (`DELETE /api/environments/:id?destroyReusableSandboxLeases=true`) > - A sandbox whose teardown failed or was interrupted is kept as a `pending_cleanup` lease, and it blocks the delete > - The cleanup sweep retries such a lease only after a cooldown of up to 5 minutes > - A consented delete therefore returned 409 `pending_sandbox_cleanup` for minutes. A caller with a shorter deadline gave up, and the environment and its sandbox stayed behind > - This pull request makes the consented delete run one teardown attempt for the environment's pending cleanups now, then re-check > - The benefit is that a consented environment delete completes as soon as the provider teardown succeeds ## Linked Issues or Issue Description **What happened?** After a restart chaos wave, the harness deleted the wave's Daytona environment with `destroyReusableSandboxLeases=true`. The server returned 409 `pending_sandbox_cleanup` every 3 seconds for the whole 120-second client deadline. A run lease had entered `pending_cleanup` after its run failed, and the sweep's retry cooldown had not passed. The environment was not deleted. **Expected behavior** With explicit consent, the delete tears down the environment's own pending sandbox cleanups and completes when that teardown succeeds. A teardown that fails, or one already in flight elsewhere, still blocks the delete. **Steps to reproduce** 1. Leave a sandbox lease of an environment in `pending_cleanup` with a future retry time. 2. `DELETE /api/environments/:id?destroyReusableSandboxLeases=true`. 3. On master, the response is 409 `pending_sandbox_cleanup` until the cooldown ends. Refs #19696 (restart recovery for creation and teardown claims; this builds on it). ## What Changed - `heartbeat/recovery.ts`: `sweepPendingCleanupLeases` accepts `environmentRetry: { environmentId, actorId }`. Like the existing run-scoped explicit retry, it bypasses the cooldown for one attempt, never takes over an in-flight attempt, and logs `environment_lease.cleanup_retried` with reason `environment_deleted`. It touches only that environment's leases. - `routes/environments.ts`: when the delete has consent and the only blockers are pending cleanup and reusable leases, it runs that retry first, then re-reads the blast radius. The existing reusable-lease destroy and the final guard are unchanged. The new dependency is a narrow, optional `retryPendingEnvironmentCleanup` option; without it, behavior is unchanged. - `app.ts`: wires the option to the existing heartbeat service instance. ## Verification - Red, then green: - `environment-routes.test.ts`: "runs the environment's pending sandbox cleanup now and deletes with explicit consent" and "keeps rejecting when the consented pending cleanup attempt does not finish" fail before and pass after. "does not run pending sandbox cleanup without consent or past another blocker" passes in both. - `heartbeat-pending-cleanup-sweep.test.ts`: "runs one attempt for a deleted environment's cleanup during its cooldown, scoped to that environment" fails before and passes after. It checks that another environment's lease and an in-flight claim are untouched, and that the activity log is written. - `sandbox-creation-operations.test.ts`: "reclaims an issue-bound creation after its run failed and the issue finished on a later run" covers another chaos finding. A creation intent bound to an issue was interrupted by SIGKILL 0.5 s after it committed, its run ended `process_lost`, and a later run finished the issue. The test fails on the code before #19696 and passes on master, so #19696 already covers this case. The test is kept as a regression. - After rebasing on master, `environment-routes`, `heartbeat-pending-cleanup-sweep`, `agent-runner-qualification-routes` and `sandbox-creation-operations` pass (192 tests). `tsc --noEmit` reports no errors in the changed files. ## Risks - A consented delete now makes provider teardown calls for pending cleanups. Those sandboxes were already queued for destruction, and the operator consented to destroy the environment's sandboxes. - One explicit attempt counts toward the lease's attempt cap, the same as a user Retry. - The delete request now waits for those teardown attempts. Each attempt uses the existing plugin timeouts. > 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 - Claude Opus 5.5 (`claude-opus-5-5`), Anthropic, via Claude Code with tool use (shell, file editing, test execution). Extended reasoning enabled. ## 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: Claude Opus 5.5 <noreply@anthropic.com>