Outside of what you describe (the little edge case issue that pop up 5% of the time), I found the biggest problem for on boarding for password managers is just

Outside of what you describe (the little edge case issue that pop up 5% of the time), I found the biggest problem for on boarding for password managers is just time. I was able to successfully get my Dad to switch to LastPass, but it took a lot of time to recontextualize what he knew about passwords before, and how to work LastPass into his daily life. After the initial setup (which involved setting up the account, showing how it works, and migrating about 25% of his passwords), he would ask me questions about it every few days. Just basic stuff like what to do when some sites don't work nice with it, LastPass not saving a password correctly, and other stuff. Once he did learn it though, it has been pretty much smooth sailing. I am only really familiar with KeePass and LastPass, but both programs have pretty terrible on boarding. LastPass has an ok 'how it works' [1] page, but what these apps really need is a guided tour/tutorial explaining what a password manager is, how to use it, and how to migrate your current password setup over to theirs. Using a password manager almost has it's own language, and teaching the users that language is the hardest part in my limited experience. [1]: https://www.lastpass.com/how-lastpass-works https://www.lastpass.com/how-lastpass-works