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I use SpiderOak for cloud backups... I like how they encrypt everything on their servers. I also want to use Truecrypt on my computer to encrypt sensitive info. Would I be able to upload these as backups to spideroak if they also encrypt everything that's uploaded?

Would there be any issues from encrypting already encrypted files, especially when it comes to getting a new computer and redownloading the files from SpiderOak?

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No, there will not be any issues encrypting already encrypted data. Encrypted data is data, and all data can be encrypted.

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Be very careful if you are talking about loading entire TrueCrypt files to SpiderOak or any other cloud services. Conduct extensive experiments to verify that SpiderOak will correctly identify which TrueCrypt file needs updating - it might or might not, depending on file size.

My own experiments indicated that once TrueCrypt files exceeded 4 or 5 GB in size, synchronization becomes very problematic. You can see a summary of these experiments at the blog: http://www.thriftslut.blogspot.com/2014/01/cloud-services-like-bittorrentsync-do.html

Basically, I found that several cloud services play nicely with many kinds of files except for TrueCrypt files.

These experiments suggest that the safest thing to do would be to mount the TrueCrypt file and then sync its contents to another folder which in turn would sync to SpiderOak. Unfortunately, this leaves you with a duplicate set of files that would be unencrypted on your computer. Or you might experiment with mounting the TrueCrypt volume and seeing if SpiderOak plays nicely with the files within the mounted volume and syncs them to the cloud. Either way, it's not a great solution to your problem and you, like me, might have to wait until cloud services develop a better one.

Hope this helps.

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