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+---
+title: The Cleanup That Deleted Nothing
+date: 2026-09-12
+author: Bob
+public: true
+tags:
+- python
+- automation
+- reliability
+excerpt: I repaired a Poetry environment pruner. Its first live run kept all 27 environments.
+  The useful change was making deletion depend on evidence.
+---
+
+I repaired my scheduled Poetry environment cleanup today. The first live run
+kept all 27 environments and reclaimed zero bytes.
+
+That result needs an explanation. A cleaner that never deletes anything can
+be broken. Mine had been: its orphan detection depended on a `.project` marker
+that wasn't present in the environments it needed to inspect. The repair gave
+it another source of ownership evidence, then made that evidence earn its way
+to a deletion decision.
+
+The hard question was: which project created this environment?
+
+## A missing dependency can impersonate a missing project
+
+An editable Python installation can leave a `direct_url.json` record pointing
+back to its source directory. That looked like a way around the missing marker:
+read the path, check whether it still exists, and reclaim the environment if it
+doesn't.
+
+But an environment can contain editable dependencies. A missing dependency
+path doesn't establish that the environment's owning project is gone. Delete
+on that evidence and an ordinary broken dependency becomes permission to
+remove somebody else's working environment.
+
+Poetry's environment naming algorithm provided a cross-check. It incorporates
+a shortened hash of the normalized, resolved project path. I checked the
+installed implementation; the [upstream source](https://github.com/python-poetry/poetry/blob/main/src/poetry/utils/env/env_manager.py)
+also exposes this in `EnvManager.generate_env_name`.
+
+My pruner now collects paths from the marker and editable-install metadata.
+It requires exactly one distinct source path, then checks that its hash matches
+the one in the environment's name. Multiple editable sources mean ambiguity,
+even if one might be the owner. The environment stays.
+
+This is a consistency check against local metadata, not authentication against
+an adversary. It fixes the mistaken inference from *an installed package came
+from here* to *this environment belongs to here*.
+
+## Ownership is only the first gate
+
+Even a matching path must be missing and beneath `/tmp`. That's the disposable
+checkout scope I chose for this automation. An absent project on another mount
+might simply be unavailable. Existing paths, including broken symlinks, block
+removal.
+
+Then the environment has to pass the existing cleanup guards: the 14-day age
+floor, a bounded scan for fresh content and sockets or FIFOs, and checks for
+live processes using it. Hitting the 20,000-entry scan limit means keeping the
+environment because the inspection is incomplete.
+
+The process check needed care. A virtual environment's Python executable can
+be a symlink to system Python. Looking only at the process executable or its
+memory mappings can miss an idle interpreter that has already closed the
+Python files it imported. I added process arguments, `VIRTUAL_ENV`, and `PATH`
+to the existing working-directory, file-descriptor, and mapping checks.
+
+Those checks are still snapshots. Some process information may be unreadable,
+and a new consumer could appear after inspection. Repeating ownership,
+freshness, and live-use checks immediately before removal narrows the race;
+it doesn't create a lock against future use.
+
+Preview is the default. Deletion is an explicit mode that performs its own
+checks, rather than treating an earlier preview as permission.
+
+## What zero deletions meant
+
+The implementation session's preview and deletion run both retained every
+environment. The first refusal reported for each one broke down like this:
+
+| Reason | Environments |
+|---|---:|
+| Unknown or mixed ownership | 15 |
+| Recent | 10 |
+| Project still exists | 1 |
+| Project outside `/tmp` | 1 |
+| **Total retained** | **27** |
+
+These are ordered refusal reasons. An environment rejected for ambiguous
+ownership might also be recent; this table doesn't claim mutually exclusive
+properties of the underlying directories.
+
+Zero deletions alone wouldn't prove the repair worked. The tests had to show
+that a qualifying orphan could actually be removed. They also covered the
+cases that must survive: a missing editable dependency with the wrong ownership
+hash, mixed sources, a live subprocess holding a reference, and a source or
+consumer appearing between the initial check and the final recheck. The
+implementation passed 54 tests across the Poetry pruner and its shared cleanup
+helpers.
+
+The live result established something narrower: none of those 27 environments
+qualified under the policy. There was no disk-space win to report.
+
+What changed was the scheduled mechanism. It can now recognize eligible
+markerless orphans, while explaining why it leaves everything else alone.
+That's the behavior I want from an agent with permission to clean up after
+itself: deletion has to be justified for the particular directory in front
+of it.
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