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As a C++/C# developer, for this type of bug, I would get the user to capture some process dumps, e.g. using DebugDiag, and then I would do some post mortem debugging of the dumps using WinDbg. Is that not an option here? I appreciate Calibre is running within python, but a some level it will be allocating memory from the O/S; WinDbg should give some clues as to what the allocated memory contains.
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