Security vs. Recovery vs. Convenience

d5q6

A few days ago, I audited the state of my own security. In cases where I have weak physical security, I wanted to make sure I also am using encryption. I also want multiple layers of security when it is not too inconvenient.

One revelation -- not a weakness in my security, but a case where I had set myself up for a bad time -- was that if my phone and my laptop were simultaneously stolen or lost, I would have been unable to log into my Dropbox to start recovering and restoring since all three passwords to my Dropbox, my email (needed to recover my Dropbox account), and my backups were long random passwords and only stored in 1Password. That would have been very uncool. I solved that by changing my Dropbox password to be something memorable and long (rather than random) and the length is not a big deal because it's not a password I'll have to type often (although now I can worry about forgetting it). I also created a backup copy of my 1Password keychain and put it somewhere safe and also encrypted the entire thing. Using Dropbox seems a lot better than Wi-Fi sync because it solves the issue of a simultaneous loss of my phone and laptop. Does this make sense to folks?

That solved, my weakest link seems to be Dropbox. If that account or Dropbox itself is ever compromised, an attacker has the opportunity to crack my 1Password master password. That leaves me with having to balance the length of my master password with how long it takes to type into my phone when I use it. It is a little annoying typing in a password long enough to be secure enough for every password, every account, and every bit of data that I have.

In other words, it would be great if there was some better solution than simply lengthening our master password over time as computing speed increases and as password cracking becomes more sophisticated. Definitely helpful would be the ability to add a second password (which would presumably be mixed or concatenated with the main master password) for sensitive accounts like FileVault keys, brokerages, etc. I know the AgileBits philosophy on multiple levels of security, but I am looking for a better way to balance security and convenience.

The only alternative to using Dropbox seems to be using Wi-Fi sync with multiple site backups (that can be accessed in the event of losing my phone and laptop). That is unfortunately a lot more work to maintain, but it does seem more secure.

Does anyone have a good alternative approach that keeps things pretty secure, but also keeps your data and online life recoverable?

D5

benfdc

I also created a backup copy of my 1Password keychain and put it somewhere safe and also encrypted the entire thing.

Not sure what you would be trying to accomplish by encrypting your 1Password keychain.

I have personally experienced the risk of using different master passwords for one's keychain on different platforms, so I am a true believer in 1Password’s current approach.

My wife and I each have put an envelope in our safe deposit box containing our respective 1Password master passwords and our Dropbox account logins. I won’t call that a perfect backup strategy, but we’re happy with it. Also, until I retired my Trēo phone last year, I would export my 1Password database to a .pdb file every now and again. AgileBits dropped .pdb export back in 1Password 3.6, but you can still open the AgileBits keychain in 3.5.

Everyone

@d5q6

That's a long wall of text that misses the obvious: Continue having a random, strong password for Dropbox, and use "Forgot My Password" to your email if you need to recover it later.

benfdc

@Everyone—That’s a short post which rests on a questionable assumption: that the password to the recovery email account is known.

I don’t know my email logins.

khad

For passwords you need to remember, we suggest using the same technique we recommend for Master Passwords.

Sometimes there are passwords you want to have in your head.