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Here's one possible approach.

Assume the attacker can modify plaintext on disk indirectly. This might be viable if e.g. the user's browser cache lives in the TC volume. (Not sure what typical TC-in-Dropbox usage patterns are, so this may or may not be realistic.)

Further assume that the attacker can observe ciphertext changes in Dropbox.

XTS is vulnerable to the same byte-at-a-time plaintext recovery attacks as ECB. This is usually irrelevant, because adaptive chosen plaintext attacks are outside the threat model considered for FDE. But in our scenario, the attacker has at least some degree of plaintext control.

The success of this attack will depend a lot on how fine-grained the attacker's control over his insertion point is, i.e. can he reliably write to the same location over and over again? Any number of components might thwart that control, so I'm not sure how easy it will be to make this work.




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