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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

3 Answers 3

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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TrueCrypt usage does impact CrashPlan. See superuser.com/a/589686/354239 –  Claus Oct 2 at 3:18
    
Ah, well to be fair his comment was about backing up an encrypted container. I wasn't clear in my answer but I was assuming the OP would be using Truecrypt in full-disk-encryption mode. With that setup there really shouldn't be any impact. I can certainly agree that things would be far less optimal if you aren't using truecrypt FDE, and just a container. –  Zoredache Oct 2 at 7:16

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

Official answer from the horses mouth: http://support.code42.com/CrashPlan/Latest/Backup/Backing_Up_TrueCrypt_Files_with_CrashPlan

Summary

  • CrashPlan can back up TrueCrypt containers, but they do not officially support this use.
  • Disable the preserve modification timestamp of file containers setting in TrueCrypt. Otherwise file changes in the encrypted container won't be backed up.
  • Everytime a TrueCrypt container is dismounted the modified date of that container is updated.
    • It's not until the dismount of the container that CrashPlan detects data changes of the TrueCrypt container.
    • The whole TrueCrypt container file will be scanned by CrashPlan. Due to data de-duplication CrashPlan might only backup part of the container.
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