Dropbox and BoxCryptor: The Dangers of Encrypting Your Digital Life

In my never ending quest to get organized, I’ve been forced to explore the world of encryption.  I set up Dropbox to use as my primary drive for all my digital document filing.  Because my Dropbox files are replicated to all my machines at home and work this has caused a security problem at work.  We’re not allowed to store sensitive data on our local drives, and my own files will set off their security scanner.  So I’m being forced to encrypt my own documents.  Normally Dropbox encrypts your files for transfer over the net and at their storage site, and I’ve considered that good enough security.  However, I started thinking what would happen if someone came into my office when I just had stepped out.  Before Windows times out and locks my machine, people could see my home files in Dropbox, so I felt it was the time to study encryption programs.

We’re being forced to use TrueCrypt and BitLocker at work, so I was having to learn about this topic anyway.  It’s a scary subject because if you’re not careful you’ll lock all your critical files into an encrypted volume and you won’t be able to open it again. 

At first I thought I just set up a TrueCrypt volume inside of Dropbox, but I read there were some issues with that.  Dropbox sees TrueCrypt as a single file, so if you have a gigabyte of data locked down, that’s a lot for Dropbox to handle over the internet.  Doing some Google research I discovered BoxCryptor.  BoxCryptor encrypts file by file, so the overhead for Dropbox is much lighter.

BoxCryptor

BoxCryptor is free for personal use as long as you only create one virtual drive.  BoxCryptor creates virtual drives.  Save something to its drives and it’s automatically encrypted.  It works with Dropbox, SkyDrive and other cloud drive services, as well as regular drives.   After you install BoxCryptor you mount the drive and use this access point to see the files unencrypted. If you don’t mount the drive and browse to the BoxCryptor folder within Dropbox you’ll see your files, but they won’t open.  And evidently, with the free version, you’ll see the filenames unencrypted, they just won’t open.  It appears if you buy the full version ($44.99), it will encrypt the filenames too, if you want.

Encrypting your files can be dangerous.  If you forget your password, kiss those precious documents goodbye.  Unless you’re a master NSA hacker, you’ll have no chance of ever opening them again.  Also, there’s a file listing in your BoxCryptor folder called .encfs6.xml.  Delete it and access to your files are long gone too.  Wow-wee – just thinking about all this makes me nervous.

Using encryption is not for the unfocused mind or scatterbrain user.

Here’s the thing.  We’re moving into an age where all our personal information is digital.  It’s our responsibility to back up our digital life.  Dropbox is a good way to do that, but Dropbox stores your files in the Cloud.  If you’re paranoid about who can see your files you’ll need to think about encryption. 

Encryption takes extra work, extra precautions and can be a very risky endeavor if you’re careless.

Some people encrypt files because they worry that Cloud storage sites might peak at the good bits in their private files.  Other people encrypt their documents because they’re afraid their computers will be stolen and bad guys will steal their identity.  Still other people encrypt files because they don’t want people at home or at the office to mess with their stuff.  Criminals encrypt files because they don’t want the police or FBI use them as evidence.  There are many reasons to encrypt files.  You have to decide if its worth the effort.

When you encrypted a folder with BoxCryptor or TrueCrypt you’ll have to create a strong password that you must not forget, and you’ll be required to save a configuration key file that you should backup carefully.   If something happens to your machine and you want to recover your files from a backup to a new machine, you’ll need that configuration key file.

If you encrypt your life its very important how you handle the password and configuration key.  If your documents are very important you might want to put your passwords and keys into your will.  If a husband encrypts all his financial records and then dies, his wife won’t be able to see them.  If you’re an author and you last manuscript is encrypted, it won’t get published unless you’ve made provisions for your heirs to unlock it.

And it’s important how you configure BoxCryptor.  If you want to just hide your files from Dropbox, just use the defaults.  If you want to hide files from people that can access to your computers (either at home, work or at the thieves hideout), then don’t configure the mount drive to automatically remember the passwords.

JWH – 2/3/13

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