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<!-- Write all pull request text in Simplified Technical English (ASD-STE100): short sentences, one instruction per sentence, simple approved vocabulary, and the active voice. --> ## Thinking Path > - Paperclip is the open source app people use to manage AI agents for work > - Agent runs use remote sandboxes held by environment leases > - #19964 settles an orphaned active lease when its holder is proven gone. It stops and keeps the sandbox, because recovery may still need its files > - Nothing destroyed that retained orphan later, so a stopped sandbox could stay at the provider indefinitely > - This pull request destroys a retained orphan once no recovery, preservation or retention obligation references it, from the reconciler pass only > - The benefit is that orphaned sandboxes do not leak, and a sandbox that recovery still wants is never destroyed ## Linked Issues or Issue Description Refs #19964 Refs #19933 **What happened?** After #19964, an orphaned sandbox is stopped and kept (`released` with a stop-and-retain receipt). No path destroyed it when recovery no longer needed it. **Expected behavior** A retained orphan is destroyed once database facts show that no obligation references it. It is never kept past the environment's retention window (the provider-attested lease `expiresAt`) only because of a soft reference. A sandbox that an active operation or a live recovery path still needs is never destroyed. **Steps to reproduce** 1. Let a run's server die after the run is terminal and before its sandbox lease is released. 2. Let the ownership settle stop and keep the sandbox. 3. Resolve the run's recovery. The stopped sandbox stays at the provider. ## What Changed - `sandbox-stop-and-retain.ts`: an ownership settle's stop intent also writes a top-level `orphanedRunLeaseRecovery` marker. The marker stays after the stop intent is removed. - `environment-retained-orphan-settlement.ts` (new): the settle for `environment_retained_orphan_sandbox`. It locks the lease row and checks database facts: - the run is terminal; - always held: native export resume, stop-and-retain intent, in-flight cleanup claim, workspace restore recovery, workspace recovery cleanup, bound source-recovery consumer, pending legacy shutdown fence, or another live lease on the same provider resource; - held while the stop receipt is a usable source (`expiresAt` not passed): pending native export or preservation fence, open recovery action on the issue, or a queued, scheduled or running run on the issue. - Then it moves the lease to `pending_cleanup` (ephemeral) with a compare-and-swap. The pending-cleanup sweep destroys it from the recorded lease. The settle never calls a provider. - `recovery/ownership-registry.ts`: the kind lists only releasable retained orphans (an SQL mirror of the checks), so a held orphan is never polled. It reports `nextDueAt` = the earliest retention-window end of a softly held orphan. - `recovery/ownership-invariant-report.ts`: an `OwnableKind` may report `nextDueAt`; the pass folds it into the report's next due time, so the reconciler wakes when the window ends. - `environment-cleanup-state.ts`: the first destroy attempt of a released orphan is due at once. ## Verification - `cd server && npx vitest run src/__tests__/environment-retained-orphan-sandbox.test.ts src/__tests__/ownership-reconciliation-report.test.ts src/__tests__/environment-run-lease-ownership.test.ts src/__tests__/heartbeat-orphaned-active-lease-sweep.test.ts src/__tests__/heartbeat-pending-cleanup-sweep.test.ts` (embedded Postgres). - Red on master, green here (tests written after the code): the settle marks the lease; an unreferenced retained orphan is destroyed through the cleanup sweep; a softly held orphan waits until its window ends and the pass reports that due time. - Counter-cases (green): never destroyed with an open recovery action, a queued run, a scheduled retry, a stop-and-retain intent, a native export resume, a workspace restore recovery, an in-flight claim, a pending legacy shutdown fence, another live lease on the resource, or an active run; a read-only pass changes nothing; a retained sandbox without the orphan marker is left alone. - Full typecheck is left to CI (local memory limit). ## Risks - A retained orphan saved by #19964 before this change has no marker, so it is not destroyed by this path. The window was short (since #19964 merged). - A held orphan with no `expiresAt` is released on the first reconciler pass after its last reference clears. If that clearing writes no signal the reconciler wakes on, the release waits for the next pass. - The SQL listing mirrors the settle's checks except the pending native export, which the settle checks in code. Such an orphan stays on the settle watch until that export settles. > 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 edit, embedded Postgres tests). ## 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>