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I'm looking into using TrueCrypt for sensitive documents that I want to store on DropBox. I wasn't sure if I should anticipate any problems if the linked computers have different operating systems - such as if the TrueCrypt volume has any sort of dependency on the underlying filesystem.

Has anyone done this? Had any problems? My gut tells me it won't be an issue, and that the TrueCrypt volume is just encrypted data, whose bits are the same regardless of filesystem, but thought I'd ask.

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up vote 2 down vote accepted

TrueCrypt containers are portable across operating systems.

Make sure you don't have the same container, located in your Dropbox folder, mounted on two systems though. This could lead to problems when Dropbox tries to sync the files.

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What happens if you try to have it mounted from 2 different computers? – Matt Apr 22 '11 at 19:45
@Matt It'll lead to simultaneous changes to the same file on different machines. I'm not sure how Dropbox handles those, you might get an error message or even lose some data. Try it and see what happens. – Daniel Beck Apr 22 '11 at 19:50
@Matt in that case I believe Dropbox will create a another copy with file name $username's filename conflicted copy. ref - – Sathya Apr 23 '11 at 4:52

There should not be any issues using TrueCrypt with Dropbox - the developers recommend this if you have sensitive data. But you will not be able to fully take advantage of certain features, such as the convenience of per-file versioning.

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I wasn't worried about DropBox + TrueCrypt so much as DropBox on different platforms, with TrueCrypt – Matt Apr 25 '11 at 15:35

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