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`with sqlite3.Connection` ends the transaction but keeps the file handle open, so every cache class leaked one handle per instance until the garbage collector happened to run. On Windows that makes the database file undeletable while the process lives (WinError 32), which broke 30 cache tests in teardown and would also block moving or clearing a cache at runtime. All eight `with <connection>` sites now go through `closing_connection()`, and a regression test asserts the schema init leaves no usable connection behind.