But CCC is already the bedrock of my backup solution, so it made sense to leverage it here, too. Of course, you can do this without CCC, as long as you don’t mind a little manual housekeeping. So if my computing situation changes and I’m ever in a pinch, I can open my encrypted documents on any computer* (I also chose to format EncryptedVolume as FAT for the same reason). I chose VeraCrypt both because it’s open source and because it’s available for Windows, Mac and Linux. That’s the best compromise I could find between convenience and security. CCC will only copy the updates, Dropbox will only upload the file difference, and nothing will be uploaded until the drive is encrypted and unmounted again. So everything is both efficient and secure during each step. And when you do have time, and/or you make important updates, use Carbon Copy Cloner to re-sync the folder to EncryptedVolume. Now you can just use your ~/Documents/Encrypted folder on an ongoing basis, and you don’t have to fool with opening encrypted volumes or anything else when you’re in a rush.

Use Carbon Copy Cloner ($40 worth it) to clone ~/Documents/Encrypted to EncryptedVolume.

Use VeraCrypt (free) to create an encrypted volume we’ll call it EncryptedVolume.

Create a folder in ~/Documents called Encrypted.

The system I’ve set up on my OS X Yosemite machine is this: If that’s enough for you, more power to you.) (Yes, I know Dropbox encrypts your data already. The problem, as I see it, is that the important stuff needs off-site backup - but the important stuff tends to be the same as the sensitive stuff, so it’s exactly the stuff that shouldn’t just be sitting on Dropbox. I spent this week searching for and experimenting with possible solutions, and I’ve now got a system in place that I’m pretty happy with, so I thought I’d share.

Dropbox encrypted folder