I’ve searched and read many similar problems and tried the solutions posted, but nothing works. I can get the server running, and access the webstart page, but when I try to claim the server it does not succeed. The wheel spins for about a minute and then times out. I’ve uninstalled and reinstalled, logged out, logged in. Any suggestions would be appreciated.Plex Media Server Logs_2019-09-15_15-06-33.zip (172.0 KB)
Next time, please specify Distro and versio, as well as version of PMS 
You log indicates, that you are having timeout errors:
Sep 15, 2019 15:05:27.897 [0x7f025e7fc700] DEBUG - HTTP requesting GET https://plex.tv/api/v2/features?X-Plex-Token= Sep 15, 2019 15:05:28.359 [0x7f023f7fe700] ERROR - Error issuing curl_easy_perform(handle): 28 Sep 15, 2019 15:05:28.359 [0x7f023f7fe700] DEBUG - HTTP simulating 408 after curl timeout
Above indicates, that you either have a bad gateway configured on your Ubuntu, or you are using slow DNS servers
If gateway is correct, the try for a small test to switch your DNS on your Ubuntu to Google DNS:
8.8.8.8 and 8.8.4.4
Then please report back
Changing my DNS servers worked >>
I figured since I could ping whatever server I wanted my networking was fine. Thanks for the suggestion!
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I’m curious is there anything to be learned from the number at the end of the curl message?
In this case it was
Error issuing curl_easy_perform(handle): 28
Thanks
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