I agree with this — I’ve “helped” a few friends transition their lives to password managers (basically just sat with them and kept suggesting sites they probably use that they might want to go change their password for — after they’ve done 5 or 6, they understand how to do it and are very likely to keep using it going forward).

I think this has to be highest benefit easy-ish thing you can do for someone to aid their computing lives in 2019 ...

Everything sites can do to help users undergo this transition would help them in the long run ...

The big password manager implementations need to do better as well — I don’t understand why iCloud Keychain doesn’t support generating random passwords that conform to the (horrific) password complexity checks you see out there in the world sometimes ... those sites are wrong to have such a broken feature but there are enough such broken sites out there that a clean workaround is needed on the password manager side ...

It would also be nice to have a solution for security questions built in — my solution is an OpenSSL command line for the random password generation and shared notes in which I record security questions and answers for sites. It’s better than actually providing real answers to security questions at least ... support for this functionality should really just be built into my password manager — the alternative likely thing is that a user will use actual answers to security questions for password reset all across the internet and this is not a thing the password managers should support their customers doing ...

I agree with you somewhat. I think my role as a developer/designer is to make sure that my forms work with pw managers. But I think encouraging users to use a manager should rest upon password managers. I can nudge them to use a secure password but the decision to write something like "please use a password manager" isn't usually my decision.

Also, let's admit it, unless you do something really crappy like remove copy-paste, forms don't exactly "not work" with managers. Most of the time, you don't have to do anything special and it would work. Some just take a bit more time because you have to cop-paste it and not autofill. But people who are already using pw managers don't just stop using it (or start memorizing their passwords) because one site can't be autofilled. They just copy paste it, at worst, they manually input it while looking at the password from their pw manager of choice.

My line about "supporting" it is a bit off. I used the wrong words. It goes to say that you should support it. Again, you have to do something really out of your way to completely block off password managers from your forms so really, I think the norm is that they support it. My thought goes more along the line of whether I should be the one to adjust when the form works on some pw manager but not on another or when the pw manager can handle other sites properly and not mine. "Working" and "handling" here means it can be autofilled (most of the time).