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I need to protect a relatively small number of sensitive files on my computer, and I'd like to use TrueCrypt for that purpose. At the same time, I have recently started using CrashPlan, and I would like my encrypted files to be backed up via CrashPlan.

What is the proper way to do this that minimizes risking corruption or recovery problems? Thanks.

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Crashplan supports encryption by itself. Why don't you just use its own encryption support? –  Ramhound Jan 14 '13 at 20:29
@Ramhound Crashplan protects the data at the destination. It doesn't do anything for the original data. –  Zoredache Jan 14 '13 at 20:37
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2 Answers

Just use Truecrypt/Crashplan normally. Usage of Truecrypt really doesn't impact Crashplan at all.

Since you are concerned about the security of your files, please do make sure that set good password for your account, and encryption keys.

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Honestly, it's much less hassle to just enable BitLocker on the drive, and then employ a highly decorated secure offsite backup solution. BitLocker is pretty-much guaranteed not to corrupt any of your files, or interfere with any of your work. All of us employees at Microsoft are required to have BitLocker enabled on our workstations at all times, and it's never caused anyone an ounce of grief that I know of.

I'm not totally sure what types of offsite backup services will meet your security needs, but if you can find a service that is FISMA and HIPAA certified, you should be good to go. These services usually have decent user interfaces, that are geared toward minimal interference with your regular operations.

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Of course you are assuming he has a version of Windows that supports BitLocker. I don't quite understand why Microsoft didn't include that in all versions of Windows. –  Zoredache Jan 14 '13 at 20:21
@Zoredache +1 Haha, indeed yes. Although MS usually tries to use features like that as leverage to squeeze people off of the "Home" editions and onto the "Enterprise" editions. –  Giffyguy Jan 14 '13 at 20:22
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