I’m looking further into your logs.
I’m seeing where, even when you’re able to transcode & play media, connection to plex.tv still fails because it cannot lookup the IP address.
Please look here. In the middle of matching media – it still fails.
Your internet service is giving you a great deal of problems.
Can you change the DNS lookup? Perhaps add another resolver like Google (8.8.8.8 or 8.8.4.4) ?
Jun 04, 2021 19:32:34.367 [0x7f3fa5ba4b38] DEBUG - [Transcode] Calculated media file path for path [metadata://art/tv.plex.agents.series_de2773c8a18beb59a363e0d03107677ac82aa00d]: ["/volume1/Plex/Library/Application Support/Plex Media Server/Metadata/TV Shows/5/2be81675e10b031c4b46348f44d45b3816f1b70.bundle/Contents/_combined/art/tv.plex.agents.series_de2773c8a18beb59a363e0d03107677ac82aa00d"]
Jun 04, 2021 19:32:34.367 [0x7f3fa5ba4b38] DEBUG - [Transcode] Calling back into ourselves for photo to transcode, optimizing the process (status: -1)
Jun 04, 2021 19:32:34.367 [0x7f3fa5ba4b38] DEBUG - [Transcode] Photo cache obtained 333050 bytes from /library/metadata/8147/file?url=metadata%3A%2F%2Fart%2Ftv%2Eplex%2Eagents%2Eseries_de2773c8a18beb59a363e0d03107677ac82aa00d&X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
Jun 04, 2021 19:32:34.368 [0x7f3fa5ba4b38] DEBUG - [Transcode] Saving original media file to /volume1/Plex/Library/Application Support/Plex Media Server/Cache/PhotoTranscoder/71/7114cf18f15a394c0398c50b944f1d9ea510f5f5.jpg
Jun 04, 2021 19:32:34.461 [0x7f3fa5ba4b38] DEBUG - [Transcode] Created thumbnail of size 360x203, has pixels: 1
Jun 04, 2021 19:32:34.468 [0x7f3fa4822b38] DEBUG - Completed: [192.168.0.3:61533] 200 GET /photo/:/transcode?url=%2Flibrary%2Fmetadata%2F8147%2Ffile%3Furl%3Dmetadata%253A%252F%252Fart%252Ftv%252Eplex%252Eagents%252Eseries_de2773c8a18beb59a363e0d03107677ac82aa00d%26X-Plex-Token%3Dxxxxxxxxxxxxxxxxxxxx&width=360&height=203 (5 live) TLS GZIP 104ms 14270 bytes (pipelined: 3)
Jun 04, 2021 19:32:35.867 [0x7f3fa47ffb38] DEBUG - Auth: authenticated user 1 as jian.jiang
Jun 04, 2021 19:32:35.867 [0x7f3fa5ba4b38] DEBUG - Request: [192.168.0.3:61533 (Subnet)] GET /library/metadata/8147/banners (5 live) TLS GZIP Signed-in Token (jian.jiang)
Jun 04, 2021 19:32:35.871 [0x7f3fa5ba4b38] WARN - Unsupported element type banners
Jun 04, 2021 19:32:35.872 [0x7f3fa47ffb38] DEBUG - Completed: [192.168.0.3:61533] 200 GET /library/metadata/8147/banners (5 live) TLS GZIP 4ms 613 bytes (pipelined: 4)
Jun 04, 2021 19:32:37.250 [0x7f3fa31b5b38] ERROR - Error issuing curl_easy_perform(handle): 6
Jun 04, 2021 19:32:37.250 [0x7f3fa31b5b38] ERROR - HTTP -6 downloading url https://metadata.provider.plex.tv/library/metadata/5d9c0871ba6eb9001fba43ff/images?episodeOrder=tmdbAiring&X-Plex-Country=US&X-Plex-Language=en-US&X-Plex-Text-Format=markdown&X-Plex-Api-Token=xxxxxxxxxxxxxxxxxxxx
Jun 04, 2021 19:32:37.251 [0x7f3fa4822b38] DEBUG - Completed: [192.168.0.3:52885] 200 GET /library/metadata/8147/posters (5 live) TLS GZIP 5017ms 756 bytes (pipelined: 9)
Jun 04, 2021 19:32:37.252 [0x7f3fa47ffb38] DEBUG - Auth: authenticated user 1 as jian.jiang
Jun 04, 2021 19:32:37.252 [0x7f3fa5ba4b38] DEBUG - Request: [192.168.0.3:52885 (Subnet)] GET /library/metadata/8147/posters (5 live) TLS GZIP Signed-in Token (jian.jiang)
Jun 04, 2021 19:32:37.392 [0x7f3fa47ffb38] DEBUG - Completed: [192.168.0.3:54157] 200 GET /player/proxy/poll?deviceClass=pc&protocolVersion=3&protocolCapabilities=timeline%2Cplayback%2Cnavigation%2Cmirror%2Cplayqueues&timeout=1 (5 live) TLS GZIP 20001ms 5 bytes (pipelined: 18)
Jun 04, 2021 19:32:37.396 [0x7f3fa4822b38] DEBUG - Auth: authenticated user 1 as jian.jiang
Jun 04, 2021 19:32:37.396 [0x7f3fa31b5b38] DEBUG - Request: [192.168.0.3:54157 (Subnet)] GET /player/proxy/poll?deviceClass=pc&protocolVersion=3&protocolCapabilities=timeline%2Cplayback%2Cnavigation%2Cmirror%2Cplayqueues&timeout=1 (5 live) TLS GZIP Signed-in Token (jian.jiang)
Jun 04, 2021 19:32:37.396 [0x7f3fa31b5b38] DEBUG - Content-Length is -1 (of total: -1).
Jun 04, 2021 19:32:42.263 [0x7f3fa5ba4b38] ERROR - Error issuing curl_easy_perform(handle): 6
Jun 04, 2021 19:32:42.263 [0x7f3fa5ba4b38] ERROR - HTTP -6 downloading url https://metadata.provider.plex.tv/library/metadata/5d9c0871ba6eb9001fba43ff/images?episodeOrder=tmdbAiring&X-Plex-Country=US&X-Plex-Language=en-US&X-Plex-Text-Format=markdown&X-Plex-Api-Token=xxxxxxxxxxxxxxxxxxxx
Jun 04, 2021 19:32:42.264 [0x7f3fa4822b38] DEBUG - Completed: [192.168.0.3:52885] 200 GET /library/metadata/8147/posters (5 live) TLS GZIP 5012ms 756 bytes (pipelined: 10)
Jun 04, 2021 19:32:42.265 [0x7f3fa47ffb38] DEBUG - Auth: authenticated user 1 as jian.jiang
Jun 04, 2021 19:32:42.265 [0x7f3fa31b5b38] DEBUG - Request: [192.168.0.3:52885 (Subnet)] GET /library/metadata/8147/posters (5 live) TLS GZIP Signed-in Token (jian.jiang)
Jun 04, 2021 19:32:42.733 [0x7f3fa31b5b38] DEBUG - Doing expensive tags write for 'Battlestar Galactica (2003)' because something changed.
Jun 04, 2021 19:32:42.750 [0x7f3fa31b5b38] DEBUG - Doing expensive tags write for 'Battlestar Galactica (2003)' because something changed.
Jun 04, 2021 19:32:42.853 [0x7f3fa31b5b38] DEBUG - Doing expensive tags write for 'Battlestar Galactica (2003)' because something changed.
Jun 04, 2021 19:32:42.868 [0x7f3fa47ffb38] DEBUG - Completed: [192.168.0.3:52885] 200 GET /library/metadata/8147/posters (5 live) TLS GZIP 603ms 2013 bytes (pipelined: 11)
Jun 04, 2021 19:32:57.397 [0x7f3fa4822b38] DEBUG - Completed: [192.168.0.3:54157] 200 GET /player/proxy/poll?deviceClass=pc&protocolVersion=3&protocolCapabilities=timeline%2Cplayback%2Cnavigation%2Cmirror%2Cplayqueues&timeout=1 (5 live) TLS GZIP 20001ms 5 bytes (pipelined: 19)
Jun 04, 2021 19:32:57.401 [0x7f3fa47ffb38] DEBUG - Auth: authenticated user 1 as jian.jiang
Jun 04, 2021 19:32:57.401 [0x7f3fa31b5b38] DEBUG - Request: [192.168.0.3:54157 (Subnet)] GET /player/proxy/poll?deviceClass=pc&protocolVersion=3&protocolCapabilities=timeline%2Cplayback%2Cnavigation%2Cmirror%2Cplayqueues&timeout=1 (4 live) TLS GZIP Signed-in Token (jian.jiang)
Jun 04, 2021 19:32:57.401 [0x7f3fa31b5b38] DEBUG - Content-Length is -1 (of total: -1).
Jun 04, 2021 19:32:57.512 [0x7f3fa47ffb38] DEBUG - Auth: authenticated user 1 as jian.jiang