Then I sadly have no more ideas, since I’m not a Mac dude 
And when said…
You did use same username in the browser as you did in the claimit script, right?
I did. I used the only email address I’ve used for my Plex account as the username.
Then sadly you’ll have to await some hardcore Mac folks to spot this thread, sorry
Are there many of those around? 
Yes, multiple
Which version of Mac OS X are you running?
If running the latest, there is a firewall tab in System Preferences -> Security & Privacy -> firewall
So you could see if that is enabled
10.14
I just checked the firewall settings and the firewall is off.
And while I doubt it, I don’t suppose it makes any difference if you try to open it from the chevron at the top of the screen:
Unfortunately, no.
And so which version of Plex Media Server are you currently running?
1.15.2
Do you have any older versions you could try?
I’ve only been using Plex for a couple months. It was working great at the start, but since all this happened, I deleted all things Plex related and tried starting from scratch several times. Any older versions I did have would be gone, and they wouldn’t have been very old regardless. Is there a way to download an older version?
Thanks to everyone that helped out on this. I finally got my server to connect with my Plex web account. Unfortunately, neither my Apple TV or my smart TV will connect to the server though. Any idea’s how I can fix this?
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