@Impman66 said in Is WinSCP or Putty necessary?:

So it begs the question, is WinSCP, Putty, or any other "file sharing" program necessary?

no, there are 3 supported methods of copying roms, and you're simply using the third: https://retropie.org.uk/docs/Transferring-Roms/#samba-shares

I just ended up using a different method, winscp on Windows, I also just mount my USB directly now instead of transferring files cause I reimage so often