Since my first Mac (an Aluminum PowerBook G4), I had relied upon SuperDuper! as my backup method for my Mac notebooks. It’s a wonderful tool, and faithfully replicates an entire volume, including making it bootable, for a worst-case drive failure scenario. I’ve used it for migrating my system to a new disk when doing disk upgrades, transferring an image to a new/replacement notebook, and just plain backups.

I’ve long since switched to using CrashPlan for my backups. CrashPlan has worked wonderfully, and saved my bacon a number of times. I use it on every computer I own. Crashplan isn’t, however, an ideal solution for migrating data to a new drive when upgrading your hard disk, simply because it’s rather slow to restore a lot of data over the network.

So, back to SuperDuper! I go, as I’m planning to add an SSD to my current MacBook Pro, and re-instate the “build a DR boot volume on an external drive” policy at home. The wrinkle is that since the upgrade to OS X Lion, both my wife’s and my notebooks are using FileVault2 for full-disk encryption. Given the sheer amount of personal information on these computers, it’s the only sane thing to do, especially when the notebooks are bound to iCloud, with Find My Mac enabled. (This gives you remote-wipe capability on your notebook, which is very useful if it’s lost/stolen.) Unfortunately, there’s no clear way to use SuperDuper! with a clean hard drive and end up with an encrypted volume that duplicates the original.

At least, not directly within SuperDuper.

All is not lost, though, as there is a way to do it, and get a fully encrypted, bootable duplicate of your FileVault2-encrypted OS volume!

In short, the procedure is:

• Install OS X Lion to your destination hard drive
• Activate FileVault2 on the new install
• Reboot to your normal startup disk
• Use SuperDuper! to “Smart Update” the destination
• Boot from the destination (SuperDuper! target) disk again
• Open System Preferences -> Security, and click on the FileVault tab.
• Click the button to enable users to unlock the volume, and enable any additional accounts (if you have the users there to type in their passwords.)
• Reboot to your normal startup disk again
• Pat yourself on the back! You did it!

I’ve tested the procedure on my old MacBook Pro, from which I’m preparing to remove the SSD to transplant it into my new MacBook Pro. It works, it boots from either volume, and they’re both encrypted (granted, with different recovery keys, as one would expect). I’ll post a followup in about a week complete with screenshots of the whole process when I migrate my OS volume to the SSD in my new MacBook Pro.

Stay tuned!