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The per-user MSI installer is stateful across runs on a persistent VM: once a version is registered, a later /quiet install no-ops and never lands at the new TargetDir, so python.exe went missing. Switch to a standalone CPython from nuget cached under LOCALAPPDATA — no registry/PATH changes, idempotent, reused across runs. A pre-existing Python 3.11 on PATH is still honoured. Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>