@modulux @alexhall for me, with NVDA, it shift+insert+insert works the same in cmd.exe and within ssh.exe inside cmd.exe.
From what I understand about terminals and SSH, SSH should not make any difference. So it's sounds like this surpasses my knowledge.
I'm following alexhall now and I was already following modulux; if you ever figure it out, I'm supercurious!
(Let me know if I can do anything more, but I think I'm useless right now.)