The Dropbox TrueCrypt Paranoia Corollary

Well, it's a week now since I started using TrueCrypt to encrypt all of my files on Dropbox, as detailed in my last post. And, I'm sad to say, after one week I'm ready to drop the encryption and go back to using Dropbox, um... unprotected. I've got a few reasons why:

TrueCrypt adds extra steps. I'm annoyingly fragile when it comes to getting into a writing frame of mind. Most anything can distract me at a critical juncture, be it a Corgi jumping in my lap for attention or that pile of laundry I forgot to pull out of the washing machine three hours ago. So having to find and mount a TrueCrypt volume before I can find and open the Word document I want to work on can actually stop me from opening that Word document. And I can't have that, now can I?

TrueCrypt nerfs Dropbox's versioning system. An obvious point I think I mentioned before, but as long as my files are in a TrueCrypt volume, Dropbox can't version them individually. For the most part, I haven't had to take advantage of this feature. Still, I've done enough development work with Subversion to know I damn well want it.

TrueCrypt slows down my syncing. I noticed this right from the get-go: with TrueCrypt, it takes Dropbox about a minute to two minutes to sync any update I make to the files in it. It's not enough to be unusable, but it's just enough to get annoying after awhile, especially if I just want to turn my computer off and go to bed after a save.

TrueCrypt actually makes me more paranoid. This is the biggie. I don't keep anything on Dropbox I would mind people looking at. Mostly it's backup copies of eBooks, evidence of CISSP CPEs I've earned, and my manuscripts. Now, it's conceivable that Dropbox is going to steal all of my shit and do nefarious things with it, but I can't imagine what. The same goes for any random hacker who breaks into my account. At worst, I'd expect to get hit with some jerk deleting everything in my Dropbox, which is why I keep offline backups.

Now, with TrueCrypt, I get the added fear that my encrypted volume might get corrupted, either from bouncing it between operating systems or by forgetting to sync updates to the volume in the correct order and having Dropbox introduce a mess of file errors. I've made that kind of screw-up before, and I don't want to do it again and have it blow away all of my files.

So, no more TrueCrypt, at least not with Dropbox. I may go back to using it to encrypt some things down the line - an In-Case-Of-Emergency file, for example - but right now it's worth more to me to have an easy time using Dropbox.

I'd go into the annoying filename quirks I ran into when I copied everything out of my TrueCrypt0 volume, but the Corg0i just jum1ped int0o my lap and star1ted1 licking my keyboard. Stop that Lina!