So here's the situation: I have a Skydrive folder that is shared with all of my colleagues at work. For added security we would like to encrypt our Skydrives with TrueCrypt. But what will happen when I upload or change a file in Skydrive? Will my colleagues, that use a different password, be able to view and edit this file? Or will TrueCrypt mess up everything with everyone else?

closed as unclear what you're asking by Adi, Xander, NULLZ, Lucas Kauffman, TildalWave Nov 28 '13 at 14:50

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  • TrueCrypt can only work by either a) encrypting the whole disk, in which case it appears just as a normal drive to the OS on top or b) creating a container file, like a ZIP archive. If a), collaboration is trivial but I doubt you can use that with cloud storage in a meaningful way. If b), you have all the headaches of trying to collaboratively edit one file with many people at the same time. I don't think this would work at all. – deceze Nov 28 '13 at 12:03

You would need to share the password as truecrypt is just a filecontainer on top of your existing filesystem. I'd strongly advice against using Truecrypt as my experience with dropbox has shown that every time you change something in the container, the complete container will need to be reuploaded.

Furthermore for the sake of confidentiality I would really refrain using personal Dropbox and Skydrive accounts for any work related matters.

Dropbox uses delta sync (so it will upload only the changes of the big file) and a change in a small file inside a truecrypt container will not result in a complete new container. https://superuser.com/a/308224/165352

Hence, a truecrypt container shared online with some service that supports delta-syncs will be fine when it comes to file uploads etc. However, you could still have the usual problem of simultaneous edit of the same file.

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