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I have read articles suggesting the use of DropBox in conjunction with a password manager database to facilitate strong, distinct passwords that can easily be used on various computers and mobile devices; however, I've also read comments claiming that this is not safe, DropBox can't be trusted, and that doing this means you're begging to be hacked or have your identity stolen.

Assuming a TrueCrypt volume with a "strong" password/passphrase on a DropBox account also with a "strong" password/passphrase, can this solution be considered safe for online backup and synchronization of sensitive information?

By "sensitive information" I am referring to password manager databases, financial software files (like Quicken), and scans of old financial documents such as purchase receipts or even tax returns.

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For data I use a WHS with varying encrypted TrueCrypt volumes depending on the level of the data which I periodically push to an external drive which is then stored in a safe. For passwords I use clipperz. – Aaron Feb 11 '11 at 19:02
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Maximum PC has a good how-to article with tips and tricks for using Dropbox. Tip 1 is using a Password program to sync your account details via Dropbox. Tip 3 is how to use TrueCrypt with Dropbox including a link to an in-depth setup article. Good food for though at the least. I would be totally confident using a TrueCrypt volume to keep personal/private information safe on Dropbox. Go for it!

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I do this. My security plan depends completely on encryption strength, Dropbox or no.

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Which is what TrueCrypt excels at. – Mircea Chirea Feb 11 '11 at 19:36
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