I can't upload media to my libraries. Please help!

Could someone please help me I’ve been trying for hours and still can’t get it to work.

I have just started with Plex and when I did so I uploaded a movie (My Spy (2020) from my downloads folder and I worked perfectly. The movie appears along with posters and movie info.
Now when I’ve gone back to it to upload more movies they don’t show in my libraries. I am almost certain that I have the naming all good so I’m not sure what the issue is.

The naming I have for the movie I am trying to upload is:
/Users/CJ/Downloads/Bedtime.Stories.2008.1080p

The naming for the movie that I have already uploaded is:
/Users/CJ/Downloads/My.Spy.2020.1080p.Bluray.DTS-HD.MA.5.1.X264

I’m not sure why it would work for My Spy and not for Bedtime Stories when the naming for My Spy looks even more confusing than Bedtime Stories.

You need to name your file correctly:

Create a separate folder, outside of your Download folder, for your movies.
Then another separate folder for TV shows, if you have any.
Then the same for music.

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