No, Core Shell version 4.0.1 has SFTP transfer functions. But not for local terminals, did you opened a local terminal shell window?
Yes, I can't upload when I connect to orbstack, but the LAN doesn't seem to work either? 192.168 network segments, must it be a public network machine?
Did you tried re-enable quick file transfer? BTW, you must re-login the SSH host before drag and drop can function.
Yang