Used KeePass and pass in the past. KeePass is nice, but has much more features than I really need. I wanted something lighter and simpler, so I migrated to pass in 2015. Even though it is nice that it relies on tools like gpg and git, it complicated things more than not. It is (was?) hard to use on every OS except Linux. And in addition to backing up the database, the gpg key now needs to be backed up, too. Password management is messy.

When searching for alternatives, I found the concept of stateless password managers. Proprietary cloud solutions are off the table for me. Because I travelled a lot in 2018, a new criterion emerged: How does bootstrapping work? How do you get any password from the database on a device that you do not own? This is obviously difficult with a traditional approach. I quickly migrated most important logins and never look back!

Besides storing passwords, a password manager should also help using them. KeePass provides Auto-Type for this. Eventually, most passwords will be used in the browser. Having a compatible browser extension became a must. Copy-pasting is a dealbreaker, because every application can read the clipboard! Most desktops support text drag and drop and on mobile, the application should provide a custom keyboard or accessibility feature.

In the meantime, I am using my own browser extension and wrote a converter plugin for KeePass to occasionally copy them (for convenience only) to my mobile. Typing the master password is cumbersome, so I use a random file (one of the dozens) in the Downloads folder as keyfile. In case of emergency or for bootstrapping, there is a web app.