Moved plex server, cannot "claim" new server

After transitioning to plex pass, I was having an issue with my local server picking up the hdhomerun on my network. At the same time I started having issues playing videos on a fire tv box on my local network, despite it working fine for months beforehand. I figured a clean install would be the simplest way to manage the issue. So while the clean install did resolve the tuner issue ('m now able to pick up & record live tv without issue), my new server on the same device simply refuses to work with the “claim server” function. As a result a lot of the advanced functionality simply won’t work. If I click on the “claim server” button it simply spins for a while and times out. Looking at the logs this seems relevant, but a search around the forums hasn’t revealed anything enlightening:

Feb 25, 2018 16:40:09.719 [0x7f11acbfe700] DEBUG - Request: [192.168.1.24:55628 (Allowed Network)] POST /myplex/claim?token=xxxxxxxxxxxxxxxxxxxx7vYWUj (18 live) GZIP Token ()
Feb 25, 2018 16:40:09.720 [0x7f11acbfe700] DEBUG - HTTP requesting POST https://plex.tv/api/claim/exchange?token=xxxxxxxxxxxxxxxxxxxx7vYWUj
Feb 25, 2018 16:40:13.034 [0x7f11bcfff700] DEBUG - Thread: Running async task started by thread 0x7f11bed23700.
Feb 25, 2018 16:40:13.894 [0x7f11b9fff700] ERROR - Error issuing curl_easy_perform(handle): 28
Feb 25, 2018 16:40:13.895 [0x7f11b9fff700] DEBUG - HTTP simulating 408 after curl timeout
Feb 25, 2018 16:40:13.895 [0x7f11b9fff700] ERROR - HTTP 408 downloading url https://plex.tv/updater/products/1/check.xml?build=linux-ubuntu-x86_64&channel=16&distribution=ubuntu&version=1.11.3.4803-c40bba82e
Feb 25, 2018 16:40:13.896 [0x7f11b9fff700] INFO - AutoUpdate: error getting data from plex.tv

I see multiple identifiers in there so I don’t know if that’s interleaved requests or what, but seeing a networking-related error and simulating a 408 seems like a problem when it’s attempting to perform the claim process. I’ve confirmed that upnp is enabled on the router; it’s a pretty bog-standard setup (static IP on 192.168.1/24) and a vanilla ubuntu 17.10 install on a poweredge t30. I’ve attached the logs if anyone else has the knowledge to dig into what’s going on here, I’d really appreciate the help as I can’t seem to take advantage of actually having a plex pass currently.

I don’t want to just blindly “bump” but this post is almost off the first page; is there anyone out there that can help? I’d hate to have to cancel my plex pass subscription after 1 month but at this point I’m not really sure what to do. I haven’t been able to get it running correctly during the entire time I’ve had my plex pass, so I don’t really get what value I’m getting out of paying for a subscription.