I have not seen this anywhere so posting in hopes it helps anyone. If this is a known issue, I apologize for posting.
After troubleshooting a couple of TV shows and movies I had, I found that if the first letter is a lower case letter, it will populate the movie/show on the server and download all the metadata…BUT when you go to play it, it will give you the spinning orange circle and never start. I deleted the file and re-added it and got the same result. It was only when I changed the first letter to a capital it started working.
Testing it 2 different ways it fixed it…
First I copied the file in a different location and then deleted the file on the server. I then changed the file to have a capital letter and saved it back to the server and let it re-download all the metadata. It played right away.
Second, instead of deleting the file, I just changed the first letter to a capital on the server itself and let it reload the info within plex and it also then played right away.
This only seemed to start happening the last 2 updates. Not sure if it is widespread or not…only know it happens on my server.
My server is running on a Windows 7 PC.