Threat models adjust over time as we become better informed. One could certainly ask why I bothered with double-encrypting, given that KeePass encrypts its vaults to begin with, but I figured double encrypting was better than single encrypting, and given the relatively high likelihood of losing a USB drive, I felt it prudent at the time. There are some issues with this approach that I encountered, such as losing the USB drive, the USB drive becoming corrupted, or not having local administrator rights on a machine that I needed to access my passwords from (required for TrueCrypt at the time, and still required by its replacement, VeraCrypt, for at least some features). I carried it around in an encrypted TrueCrypt volume that lived on a portable USB drive.

Years ago (read: 2010-2011ish?), I used KeePass. In that light, these posts are also about why I made the decision to stop trusting my passwords to LastPass after three years of use, why 1Password is not currently a reasonable alternative (in my opinion), and why I ultimately went back to using KeePass and my own syncing solution. This is one step in my ongoing quest to improve the security of my information and systems. These posts are to documement my overall experience with different password storage solutions, and an amateur evaluation that I performed from the perspective of a customer/user of different password vault options.

LastPass versus 1Password versus KeePass, part 1

Keepass professional vs classic