You need to SSH into your PI. Easiest is a program called putty, but you will need to google for a tutorial if not familiar with the process. Another app is WinSCP
WinSCP is a poor choice for using CLI.
Quick instructions for use of PuTTY in our wiki https://osmc.tv/help/wiki/console
Yes, for CLI it seems to have issues, but it does have a icon to use Putty. I do like WINSCP for moving files back and forth though.