It's somewhat easier with Bash on Ubuntu on Windows, tho kinda broken (because the copy to clipboard feature doesn't work out of the box unless you're running an X server).

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.