One backup is never enough...

I had trouble with my backup lately when switching to a new MacBook. I tried restoring the data to the new machine as a test.

The WD Passport software restore failed (it restored a 6-month old version of my files for some reason). Since the WD Passport software doesn't have a backup tool for Mac, I tried to configure it with Timemachine instead. The WD Passport USB drive died. I reformatted it from Windows: impossible to write to it any more. Surface tests with the WD diagnostic tools failed. It probably didn't like the whole traveling thing.

The Mozy restore worked fine.

So here is the new setup:

Off-site backup

• Automatic backup to Mozy using local encryption with passphrase. 

On-site backup

• Automatic backup to a USB drive with TimeMachine and Apple encryption.
• Manual backup every now and then of sensitive files to a USB key protected with Truecrypt. It's good to have a simple copy of your important data. A simple, straight copy that doesn't require backup software. Because DVDs are out, a simple USB key should do.

The main disk is encrypted with FileVault. 

I'm still using Mozy but I'm considering moving to Backblaze that also offers local encryption with a passphrase that no one else knows and unlimited storage. Also Backblaze claims to be able to backup data from a USB drive as well without getting confused. I tried doing this with Mozy and it got mad, deleting all my files from the server as soon as I unplugged the drive.

Keep your data safe while traveling

Before leaving London for a 6 month break I sold my desktop and replaced it with a MacBookPro. The MBP has become my main computer and because I'm traveling, I had to review the whole backup routine… The likelihood of having it stolen or lost on the beach is quite high (compared to having my flat broken into for instance).

After trying a few things I came up with this: I sorted out my data into two groups, sensitive data and mobile data.

Sensitive data
Stuff you really don’t want someone to steal from you.
That includes budget spreadsheets, bank statements, receipts, health documents…

• Store on local drive
• Encrypt with TrueCrypt (Windows) or Filevault (MacOs). You can forget the Filevault password, the only purpose of encrypting the data on the local drive is to prevent it from being accessed by someone who steals the laptop. 
• Back-up manually to external HD with hardware encryption (such as My Passport which comes with a built-in backup software WDSmartware).
  This external HD should always stay in the room, or in the hotel safe. If the main laptop gets stolen or crashes, this is the first line of defense. Of course the HD itself could be stolen that’s why data should be encrypted with a password that you remember.
• Backup off-site automatically with a service that allows local encryption (such as Mozy)
  Local encryption technology exists so there is no point taking the risk of trusting the cloud storage provider to encrypt the really sensitive data for you. Just don’t forget the password.

Mobile data
Stuff you need with you all the time, files used often and on-the-go that are less sensitive: photos, travel itineraries, hotel bookings, flight tickets, travel insurance certificate, passport scans, ebooks.

• Must be quickly synchronised across devices (iPhone, iPad, PC, MacBook, web). Dropbox is good for that. iCloud not so much...
• Encrypt the offline cache with OS encryption. Encrypt the Dropbox folder with TrueCrypt/FileVault so that the files stored offline cannot be accessed if the laptop gets stolen.

Notes:

Why use TrueCrypt for sensitive data under Windows and not EFS?

The backup systems I tried (WDSmartware and Windows8 File History) don't know how to save EFS-encrypted files. Mozy knows how to save EFS-encrypted files. But when it restores them, they're still encrypted with EFS. So if you lose your laptop and don't have the EFS keyfiles, you lose your data. I find EFS a bit cumbersome because if you're serious about testing it, you have to do a restore to a totally different system to make sure that you're able to decrypt the EFS files, save the keyfiles to USB drives, blah blah blah. I know I’ll just get it wrong so I prefer using TrueCrypt.

Don't use Mozy to save data stored on the external HD

Mozy is really bad at saving data located on a removable drive (such as an external HD). Mozy starts automatically. If the drive is not connected at the time when Mozy starts, Mozy thinks the files were deleted from the machine and it marks them as deleted from the server, which is a bit rough.