While I was enamored with 1Password (and still am) the biggest hurdle to it’s adoption is that I own a PC and a Mac (remember?). Syncing the password database between computers is therefore a necessity, and syncing across operating systems (XP/7 to OS X and vice versa) even moreso. This was certainly doable with KeePass and KeePassX, although KeePassX didn’t support a global auto-type hotkey. A password storage system is rendered virtually useless if every single time I have to log into a different web page I have to bring up the KeePassX window; copy my information to the clipboard, bring the focus back to FireFox, and type it in. Well, good news! An updated (albeit currently unsupported) version of KeePass (based on v0.4.1) adds auto-type functionality!

So now that we have auto-type everywhere, how to sync so we can use our KeePass databases everywhere we go? Well it’s very easy.

1.) If you aren’t using Dropbox yet, start. Go to Dropbox, set up and account, download the software, and set it up so both (or however many you have) machines are synced. Create a folder somewhere in your Dropbox scheme (by default under Documents -> My Dropbox) called “KeePass.”
2.) Download and install KeePassX (Mac) here. Download and install KeePass Classic (Windows) here. Note: We need to download the “classic” version because KeePassX still uses the old .kdb format instead of the new .kdbx. While we can set triggers in the new Windows version to automatically pop out a .kdb version AND a .kdbx every time we edit a password on that computer, we can’t edit .kdb’s on the Mac and automatically import them into KeePass on the Windows box. And that makes syncing unfun.
3.) On the Windows box (you can do it the other direction, too, but I found the Windows KeePass interface to be a bit more intuitive) open KeePass and create a new database. Set a “master password” and repeat. Don’t let this password suck too much; after all, you’ll be MINIMIZING the number of passwords you have to remember– at the very least you can do a good job coming up with a solid password that gives access to– well– everything else. Use a key file, too, if you’d like, but I find it unnecessary; it’s always something you can add later.
4.) Click “save as” and save the .kdb file to the directory you previously created within your dropbox scheme. Temporarily close KeePass on Windows and open KeePassX on the Mac. Browse to the newly created (and synced) database file and click open. Enter password. Try creating a few keys. Save. Close.
5.) Re-open the Windows version. Now you should only be prompted for the password (no browsing needed) and you should see your KeePass passwords in Windows. Congrats; you’ve done the heavy lifting!

A few notes; this will work between a PC/Linux or Linux/Mac as well. The same general steps apply although you will need the KeePass repo for your Linux flavor or you can compile from source. If you are a Linux user, I figure you probably don’t really need directions on how to do that. Second, KeePass (and therefore KeePassX) don’t automatically update the database while the program is running. Therefore, when you are adding keys be careful not to add different keys on different computers while both are still open. Dropbox handles conflicts well but you will lose some keys depending on what was open and what was being edited at the time. As a rule of thumb, when I first started migrating to KeePass I never had it running on more than one computer at a time. Once you have a stable database, it’s fine to have multiple instances going at once (it will typically ask to open in “read-only” anyways).

You can turn auto-type on and off by doing the following:
Windows: Tools -> Options -> Advanced tab -> Auto-Type button (lower right).
Mac: KeePassX -> Preferences -> Advanced

Some final notes to get auto-type running flawlessly on your computer. As a general practice, I had two lines to the comments of every key.

Auto-Type-Window: *balloflightning.com*

This aids KeePass/X in finding the window you want to auto-type in. I’ve found great success with the Firefox add-on “Hostname” which puts the domain name of the current web-site in the title bar. It may add a bit of clutter to your windows, but it provides you a surefire way to make sure KeePass/X is only auto-typing in the proper Firefox window/tab. The ‘*’ are wildcards, signifying KeePass/X will find whatever window has XXXXX balloflightning.com XXXXX in it. Obviously, you change the hostname between the ‘*’ to whatever key you are storing (i.e., paypal.com, ebay.com, etc.)

Auto-Type: {USERNAME}{TAB}{PASSWORD}{ENTER}

This is the custom sequence for the target window. {USERNAME} and {PASSWORD} are the stored username and password, {TAB} is… well… tab and {ENTER} is also self-explanatory. In some cases you may be forced to modify this (for example, I have to add a {TAB} after {USERNAME} every once in a while because the websites have a “click here to remember me” form.

Some people will find that in OS X, tabbing will result in certain portions of forms (checkboxes, radio buttons, dropdowns, etc.) being skipped. This creates a bit of a problem here because the sequences will then not match between Windows and Mac. Solution?

1.) Open System Preferences
2.) Go to Keyboard & Mouse
3.) Select “All controls” for full keyboard access

For a Firefox-only solution, you can also add / change the accessibility.tabfocus Firefox option via about:config to one of the following: 3 to be able to tab to form controls or 7 to be able to tab to everything