Server problems

Since Mac are a little bit unix-y, my first guess would be permissions or ownership. Also, maybe the Plex server didn’t get notification of the new files. I’ve never used a Mac, but if you go into a terminal, is there a “touch” command? On my linux system, I’d so something like “touch *.mp4” to alter the file modification times. You could also do a Plex Dance, but the touch command is a bit quicker.