Here you go. Looks like it times out when trying to talk to plex.tv
Jun 24, 2023 05:51:15.201 [139957399448376] DEBUG - Completed: [192.168.1.73:54673] 200 GET /media/providers (5 live) #166 GZIP 1ms 1242 bytes (pipelined: 12)
Jun 24, 2023 05:51:15.310 [139957370166072] DEBUG - Request: [192.168.1.73:54673 (Subnet)] POST /myplex/claim?token=xxxxxxxxxxxxxxxxxxxxJRmo6g (5 live) #168 GZIP Token ()
Jun 24, 2023 05:51:15.310 [139957370166072] DEBUG - [Req#168/HCl#92] HTTP requesting POST https://plex.tv/api/claim/exchange?token=xxxxxxxxxxxxxxxxxxxxJRmo6g
Jun 24, 2023 05:51:16.573 [139957384919864] DEBUG - [HttpClient/HCl#8f] HTTP simulating 408 after curl timeout
Jun 24, 2023 05:51:16.573 [139957354462008] ERROR - [Req#157] HTTP 408 downloading url https://plex.tv/updater/products/5/check.xml?build=linux-x86_64&channel=16&distribution=debian&version=1.32.4.7195-7c8f9d3b6
Jun 24, 2023 05:51:16.573 [139957356571448] INFO - [Req#157] AutoUpdate: error getting data from plex.tv
Jun 24, 2023 05:51:16.574 [139957399448376] DEBUG - Completed: [192.168.1.73:54675] 200 PUT /updater/check?download=0 (5 live) #157 GZIP 15001ms 312 bytes (pipelined: 5)
Jun 24, 2023 05:51:30.315 [139957384919864] DEBUG - [HttpClient/HCl#92] HTTP simulating 408 after curl timeout
Jun 24, 2023 05:51:30.315 [139957370166072] DEBUG - [Req#168] MyPlex: Did token exchange for claim (returnCode: 408)
Jun 24, 2023 05:51:30.316 [139957370166072] DEBUG - [Req#168] MyPlex: Got a token poked, let’s act on it.
Jun 24, 2023 05:51:30.316 [139957370166072] DEBUG - [Req#168/HCl#94] HTTP requesting GET https://plex.tv/api/v2/user/privacy?X-Plex-Token=
Jun 24, 2023 05:51:43.258 [139957377551160] DEBUG - BPQ: [Starting] → [Processing]
Jun 24, 2023 05:51:43.258 [139957377551160] DEBUG - BPQ: creating new background playqueue
Jun 24, 2023 05:51:43.259 [139957377551160] DEBUG - BPQ: generating queue items from 0 generator(s)
Jun 24, 2023 05:51:43.259 [139957377551160] DEBUG - BPQ: generated 0 item(s) for queue
Jun 24, 2023 05:51:43.260 [139957377551160] DEBUG - PlayQueue: 0 generated IDs compressed down to a 20 byte blob.
Jun 24, 2023 05:51:43.260 [139957377551160] DEBUG - PlayQueue: 0 generated IDs compressed down to a 20 byte blob.
Jun 24, 2023 05:51:43.260 [139957377551160] DEBUG - BPQ: [Processing] → [Idle]
Jun 24, 2023 05:51:45.319 [139957384919864] DEBUG - [HttpClient/HCl#94] HTTP simulating 408 after curl timeout
Jun 24, 2023 05:51:45.319 [139957370166072] WARN - [Req#168] [Analytics] Couldn’t get analytics privacy settings. Trying again soon.
Jun 24, 2023 05:51:45.319 [139957370166072] DEBUG - [Req#168/HCl#95] HTTP requesting GET https://plex.tv/api/v2/release_channels?X-Plex-Token=
Jun 24, 2023 05:51:53.733 [139957282741048] DEBUG - SSDP departed after not being seen for 21.866549 seconds: 192.168.1.12 (SHIELD)
Jun 24, 2023 05:51:53.873 [139957360790328] DEBUG - [NSB/SSDP] Parsing SSDP schema for http://192.168.1.12:8008/ssdp/device-desc.xml
Jun 24, 2023 05:52:00.324 [139957384919864] DEBUG - [HttpClient/HCl#95] HTTP simulating 408 after curl timeout
Jun 24, 2023 05:52:00.324 [139957370166072] WARN - [Req#168] [AutoUpdateRequestHandler] Couldn’t get update channels. Trying again soon.
Jun 24, 2023 05:52:00.324 [139957370166072] DEBUG - [Req#168/HCl#97] HTTP requesting GET https://plex.tv/api/v2/features?X-Plex-Token=
Jun 24, 2023 05:52:15.328 [139957384919864] DEBUG - [HttpClient/HCl#97] HTTP simulating 408 after curl timeout
Jun 24, 2023 05:52:15.328 [139957370166072] WARN - [Req#168] FeatureManager: Couldn’t get features. Trying again soon.
Jun 24, 2023 05:52:15.329 [139957401557816] DEBUG - Completed: [192.168.1.73:54673] 500 POST /myplex/claim?token=xxxxxxxxxxxxxxxxxxxxJRmo6g (4 live) #168 GZIP 60019ms 522 bytes (pipelined: 13)
Jun 24, 2023 05:52:15.329 [139957370166072] DEBUG - Request: [127.0.0.1:59358 (Loopback)] GET /servers (4 live) #159 GZIP Token ()
Jun 24, 2023 05:52:15.330 [139957399448376] DEBUG - Completed after connection close: [127.0.0.1:59358] 200 GET /servers (4 live) #159 GZIP 0ms 0 bytes
Jun 24, 2023 05:52:15.362 [139957370166072] DEBUG - Request: [192.168.1.73:54673 (Subnet)] GET /services/defaultLibraries (4 live) #175 GZIP
Jun 24, 2023 05:52:15.362 [139957356571448] DEBUG - Request: [192.168.1.73:54766 (Subnet)] GET /library/sections (4 live) #174 GZIP
Jun 24, 2023 05:52:15.363 [139957399448376] DEBUG - Completed: [192.168.1.73:54673] 200 GET /services/defaultLibraries (4 live) #175 GZIP 1ms 350 bytes (pipelined: 14)
Jun 24, 2023 05:52:15.367 [139957399448376] DEBUG - Completed: [192.168.1.73:54766] 200 GET /library/sections (4 live) #174 GZIP 5ms 392 bytes (pipelined: 1)
Jun 24, 2023 05:52:15.411 [139957384919864] DEBUG - [HttpClient/HCl#96] HTTP/1.1 (0.1s) 200 response from GET http://192.168.1.12:8008/ssdp/device-desc.xml
Jun 24, 2023 05:52:15.411 [139957360790328] DEBUG - [NSB/SSDP] found 1 SSDP devices via http://192.168.1.12:8008/ssdp/device-desc.xml
Jun 24, 2023 05:52:15.411 [139957360790328] DEBUG - [NSB/SSDP] SSDP arrived: 192.168.1.12 (SHIELD)
Jun 24, 2023 05:52:15.503 [139957289069368] DEBUG - [Req#168/MediaProviderManager] we had 1 cloud providers online, we now have 1
Jun 24, 2023 05:52:15.503 [139957289069368] DEBUG - [Req#168/MediaProviderManager] cloud provider (Metadata) is online and available
Jun 24, 2023 05:52:16.364 [139957356571448] DEBUG - Request: [192.168.1.73:54673 (Subnet)] GET /media/providers (4 live) #178 GZIP
Jun 24, 2023 05:52:16.365 [139957401557816] DEBUG - Completed: [192.168.1.73:54673] 200 GET /media/providers (4 live) #178 GZIP 1ms 1242 bytes (pipelined: 15)
Appreciate the help
…after months with this issue I finally claimed the server. I changed my DNS from google to quad 9 because of the connection issue. Is this all it took to solve it? I guess. Maybe Alphabet hates plex.