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If you store an image with executable code in it on Dropbox via Truecrypt, how many times will you potentially run it out of that image?

Again: we are talking about properties that cryptographically sound systems simply don't have. And if you're using Dropbox as your backing store, and not a physical drive, there is no reason to accept those properties!

If I store a program on Dropbox, I might run it many times. Thousands? Millions to be generous? But if the attacker has to do a brute force search which relies on me executing each different tampered version of the program, that's probably too small of a number.

The reason to accept sub-optimal properties in this case is convenience. Truecrypt is popular and has a nice interface. Using it with Dropbox gives much better security than not using it with Dropbox. It's not perfect, but I still don't think we have any practical attacks against such a scenario.

I agree that having stronger crypto there is however possible and desirable.

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