On the surface endpoint encryption is pretty straightforward these days (WAY better than when I first covered it 8 years ago), but when you start matching all the options to your requirements it can be a tad confusing.

I like to break things out into some simple categories/use cases when I’m helping people figure out the best approach. While this could end up as one of those huge blog posts that ends up as a whitepaper, for today I’ll stick with the basics. Here are the major endpoint encryption options and the most common use cases for them:

  • Full Drive Encryption (FDE): To protect data when you lose a laptop/desktop (but usually laptop). Your system boots up to a mini-operating system where you authenticate, then the rest of the drive is decrypted/encrypted on the fly as you use it. There are a ton of options, including McAfee, CheckPoint, WinMagic, Utimaco, GuardianEdge, PGP, BitArmor, BitLocker, TrueCrypt, and SafeNet.
  • Partial Drive Encryption: To protect data when you lose a laptop/desktop. Similar to whole drive, with some differences for dealing with system updates and such. There’s only one vendor doing this today (Credent), and the effect is equivalent to FDE except in limited circumstances.
  • Volume/Home Directory Encryption: For protecting all of a user’s or group’s data on a shared system. Either the users home directory or a specific volume is encrypted. Offers some of the protection of FDE, but there is a greater chance data may end up in shared spaces and be potentially recovered. FileVault and TrueCrypt are examples.
  • Media Encryption: For encrypting an entire CD, memory stick, etc. Most of the FDE vendors support this.
  • File/Folder Encryption: To protect data on a shared system- including protecting sensitive data from administrators. FDE and file folder encryption are not mutually exclusive- FDE protects against physical loss, while file/folder protects against other individuals with access to a system. Imagine the CEO with an encrypted laptop that still wants to protect the financials from a system administrator. Also useful for encrypting a folder on a shared drive. Again, a ton of options, including PGP (and the free GPG), WinMagic, Utimaco, PKWare, SafeNet, McAfee, WinZip, and many of the other FDE vendors (I just listed the ones I know for sure).
  • Distributed Encryption: This is a special form of file/folder encryption where keys are centrally managed with the encryption engine distributed. It’s used to encrypt files/folders for groups or individuals that move around different systems. There are a bunch of different technical approaches, but basically as long as the product is on the system you are using, and has access to the central server, you don’t need to manually manage keys. Ideally, to encrypt you can right-click the file and select the group/key you’d like to use (or this is handled transparently). Options include Vormetric, BitArmor, PGP, Utimaco, and WinMagic (I think some others are adding it).
  • Email Encryption: To encrypt email messages and attachments. A ton of vendors that are fodder for another post.
  • Hardware Encrypted Drives: Keys are managed by software, and the drive is encrypted using special hardware built-in. The equivalent of FDE with slightly better performance (unless you are using it in a high-activity environment) and better security. Downside is cost, and I only recommend it for high security situations until prices (including the software) drop to what you’d pay for software. Seagate is first out of the gate, with laptop, portable, and full size options.

Here’s how I break out my advice:

  • If you have a laptop, use FDE.
  • If you want to protect files locally from admins or other users, add file/folder. Ideally you want to use the same vendor for both, although there are free/open source options depending on your platform (for those of you on a budget).
  • If you exchange stuff using portable media, encrypt it, preferably using the same tool as the two above.
  • If you are in an enterprise and exchange a lot of sensitive data, especially on things like group projects, use distributed encryption over regular file/folder. It will save a ton of headaches. There aren’t free options, so this is really an enterprise-only thing.
  • Email encryption is a separate beast- odds are you won’t link it to your other encryption efforts (yet) but this will likely change in the next couple years. Enterprise options are linked up on the email server vs. handling it all on the client, thus why you may manage it separately.

I generally recommend keeping it simple- FDE is pretty much mandatory, but many of you don’t quite need file/folder yet. Email is really nice to have, but for a single user you are often better off with a free option since the commercial advantages mostly come into play on the server.

Personally I used to use FileVault on my Mac for home directory encryption, and GPG for email. I then temporarily switched to a beta of PGP for whole drive encryption (and everything else; but as a single user the mail.app plugin worked better than the service option). My license expired and my drive decrypted, so I’m starting to look at other options (PGP worked very well, but I prefer a perpetual license; odds are I will end up back on it since there aren’t many Mac options for FDE- just them, CheckPoint, and WinMagic if you have a Seagate encrypting drive). FileVault worked well for a while, but I did encounter some problems during a system migration and we still get problem reports on our earlier blog entry about it.

Oh- and don’t forget about the Three Laws. And if there were products I missed, please drop them in the comments.