KeePass & Dropbox, Teaming Up For Secure And Safe Passwords

Ever since I started using the Internet, sites have been asking me to register and log in. Usually I’d have a few secure passwords for sites that really mattered and a number of throwaway passwords that I reused on several different sites where I didn’t really care too much about security. Those sets of passwords changed over time and also the importance of sites changed. Fast forward 15 years and my login IDs and passwords have become a mess.

I’ve now found the perfect solution in KeePass, a password manager that securely stores all my passwords and makes it easy to have a different one for every site. I’ve combined it with Dropbox to synchronize everything across computers.

In principle, KeePass is a very basic database program. It consists of a list filled with login/password combinations. There are many functions to keep that list organized and clean. However, what is really important are all the options to keep this information secure. The password database itself can be encoded with several different algorithms and security levels. And if you copy a password to your clipboard, it will only stay there for a limited number of seconds.

By itself, KeePass is already a useful program, but there are a few shortcomings

  • Storing all your passwords in one single file creates one gigantic single point of failure. Not only should you make the master password that opens the file very secure, you should also back up the file religiously.
  • The passwords that KeePass generates are secure, but they are also impossible to memorize (well, I know a few guys …). So you need KeePass and your password database wherever you are going to log in to sites.

I’ve solved both problems with two additional tools

  • Dropbox (previous coverage). If you trust the guys at the Dropbox serverfarm, the program will securely transmit (and store) your database across different platform (and even if you don’t trust them, the password file is always encoded).
  • KyPass by Kyuran lets me take my password with me on my iPod Touch wherever I go. KyPass also has synchronization with Dropbox build in (*). Something which is lacking from all of the competition.

There’s still one thing left that I’d like to see solved to complete my perfect password setup:

  • There are a few plugins for Firefox that should be able to easily fill login forms. However, I tried to first one on the list and was so disappointed I haven’t tried again. In principle, this sounds like a good idea, so I’ll be back on it.

(*) By default KyPass expects the Keypass files in a folder named “Crypted” on your Dropbox account. You can change this folder via the iPods settings screen, but not from the application itself. A fact that isn’t documented. The author was very helpful in quickly solving this issue, so 2 thumbs up for support.

Updated on July 11th 2011 to add KyPass, the perfect iOs companion.

(image credit)