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All of the question I would like to ask is pretty much contained in the title...

I have a couple Truecrypt-encrypted folders on OS X, where I keep some .tex documents I edit in TeXShop, and the question is: does TexShop 'bleed' information? Does it store temporary files anywhere else on the system? Filenames, filecontents etc.

Cheers!

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According to this article, TeXShop creates temporary files when converting to PDF.

Depending on your version of Mac OS X, you can use File Monitor to watch for changes and investigate exactly what files TeXShop creates when you use it.

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