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@samueldavidkeyes
Constantly had an issue with this on some old cranks with a bit of a bent taper, so the bolt was constantly being undone by the microflexing every turn. I just put a smidge of araldite on the inside thread of the bolt, then tightened it up loads. It was totally undoable, though don't do this unless the crank and bb are sufficiently beaterish.