I guess the question is if you could do bad things to truecrypt itself this way, or if it would be easier to rely on user intervention. There is also "what can be done by Dropbox itself" (potentially via court order) vs what could be done by mitm (not sure what protections Dropbox has against this; if it uses the host ca certs to authenticate vs in app cert pinning (which is obvious and good), etc.
Being able to "glitch" someone's truecrypt volumes without even compromising the crypto could lead to fun. Also, OS/file system cruft on the level above, essentially the equivalent of an .htaccess file, could be fun.
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I guess the question is if you could do bad things to truecrypt itself this way, or if it would be easier to rely on user intervention. There is also "what can be done by Dropbox itself" (potentially via court order) vs what could be done by mitm (not sure what protections Dropbox has against this; if it uses the host ca certs to authenticate vs in app cert pinning (which is obvious and good), etc.
Being able to "glitch" someone's truecrypt volumes without even compromising the crypto could lead to fun. Also, OS/file system cruft on the level above, essentially the equivalent of an .htaccess file, could be fun.