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Fix a bunch of low-severity issues detected by an LLM.

Using contextlib, we can emulate a `with` statement for multiple files,
such that there is no resource leak if an exception occurs before the files
are closed.
@jakobnissen jakobnissen added the DO NOT SQUASH Each commit in this PR should be kept individually label Jan 9, 2026
We know the shape at compile time, but let's check it for good measure
@jakobnissen jakobnissen merged commit aa42e12 into master Jan 9, 2026
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