@alexhall I have the same problem. If you ever work out a solution let us know.
@modulux @alexhall this is very strange. (I'm sighted and not using a screen reader, so I might say stupid things.)
I just tried Windows 11 + cmd.exe (which opens Windows Terminal for me) + ssh.exe; I could paste with shift+insert on a remote session; the hotkeys seem to be handled by Windows Terminal.
Windows Terminal allows changing the paste hotkey, I tried changing it to ctrl+j and it worked too.