But yeah, I kinda don't like using Gpg4Win with Cygwin, which is what I'm guessing you've used too.
With the "Creators Update" there's now a `clip.exe` to which one can pipe so maybe it's not too hard to update Pass, which is itself just a Bash script.
i Really like the idea of pass, but ill never accept copy pasting logins/passwords again. they'll need to be automatically inserted on a matching website. everything else is too much manual overhead for my taste.
Copying and pasting may be annoying, but it's much safer, especially if you use a program that will autoclear your clipboard for you (KeePass 2 does this after 12 seconds by default).
https://addons.mozilla.org/en-US/firefox/addon/passff/
https://addons.mozilla.org/en-US/firefox/addon/pass-manager/
pass got linux covered (both chrome and firefox), but doesn't really work for winndows.
android is really tiresome as well, as there is no way to skip my long masterpassword in favour of a fingerprint. I know, its not easy to implement that feature securely.
Today I found this, need to check it out: https://github.com/Baggykiin/pass-winmenu
I understand it's the standard UNIX password manager, so I suppose I don't have a ton of room to complain, and most of my computers are Mac or Linux, so it's not a huge deal, but I think it increases the barrier of entry a ton of people.
That said, I think Pass is awesome, and having my passwords stored in Github makes me really happy.