Cool Beans

Lots of security-conscious users say we should use whole disk encryption. It prevents files from being read when you're not logged in. This is good protection if your computer is lost or stolen. If not used, tools like Knoppix, Slax, or DamnSmallLinux can easily be used to boot a fully functioning operating system (from, say, a CD or USB key) and view your files' contents.

Even deleted files are not truly deleted. They are not listed but also not fully removed from the disk. Typically, they exist without a file pointer to their location, so an undelete program or disk scanner can easily recover and/or view them.  The only remedy to this is to "wipe" them, and people don't typically expend the extra steps to perform a file wipe.

So your hard disk in its default state presents problems. Aside from oft-cited airport laptop searches, it's just not cool to have your files ready to be read by almost anyone with a USB key or bootable CD. Hence the push for encrypting everything on the whole disk. This is good for a few reasons:

• It's ubiquitous: You don't have to think about it and the drive is protected.
• There's little performance hit for doing this.
• It's free and easy to configure.
  
• The default state of files is secure, a.k.a. fail-secure.
  

But this is a bit of overkill, in my opinion. If you also like things like versioning, snapshots, and incremental backup (e.g. Apple's Time Machine), whole-disk encryption forces a choice: Do you want smart automatic backups? Or do you want to backup your entire disk volume (BIG!) each and every time?

I puzzled over this for a while, sticking with whole-disk encryption while not having a safe backup somewhere. I figured privacy and security were more important than the risks of data loss. (Huh?)

But with a new computer, I realized that automated unattended backups gave great peace of mind. How could I have incremental, optimized, regular scheduled backups while having some form of data privacy and security? One option was to create various encrypted volumes using Disk Utility or Truecrypt. But this was cumbersome, manual (needing me to remember to mount and unmount a volume all the time), and still didn't address my backup concerns.

I also realized that every single file on the computer does not need to be encrypted. Many files, like application libraries, everyday documents, publicly shareable media, etc. do not need high encryption. Just don't mix tax forms and healthcare PDFs with the latest lolcats jpegs saved to the Documents folder.

It was then that I happened upon Tao Effect Espionage.

Espionage is a customizable encryption tool that can secure areas you choose. It takes advantage of the sparsebundle and sparseimage functionality of OSX, but automates the process so you don't have to think about encryption. This forces you to keep your files organized, protect sensitive ones, and keep the rest of your system and non-sensitive files available for simple backups. Each time you want to access an important doc, a prompt gets your authorization, and you are in. Otherwise, it's fail-secure.

It even works on the Application-level. So let's say you want to password-protect and encrypt your email. This is not trivial in OSX. But with Espionage you can configure your Mail app to be protected, and it will unlock and lock the mail directories whenever the app is opened or closed!

Truth-in-advertising: There's a little trickery that needs to happen with Espionage and Time Machine. Espionage has its own backup functionality, and it's best to ignore protected directories in the Time Machine preferences. But I believe even with this slight config, the application is a great balance between keeping files secure, and keeping things simple, available, and smartly backed up.

In so many words of this article, it's easy to resist and do nothing. But don't do nothing! Keep your files both secure and backed up! You no longer have to choose one or the other; use Tao Effect Espionage.