Your network is a mess.
Jan 12, 2021 09:03:14.652 [0x7f430035b740] DEBUG - NetworkInterface: Notified of network changed (force=0)
Jan 12, 2021 09:03:14.652 [0x7f42f4e11700] DEBUG - PublicAddressManager: Obtaining public IP.
Jan 12, 2021 09:03:14.653 [0x7f42f4e11700] DEBUG - HTTP requesting GET http://plex.tv/pms/:/ip
Jan 12, 2021 09:03:14.653 [0x7f42f4835700] DEBUG - NAT: UPnP, attempting port mapping.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - Detected primary interface: 0.0.0.0
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - Network interfaces:
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - * 1 lo (127.0.0.1) (loopback: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - * 3 eth0 (192.168.0.240) (loopback: 0)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - * 4 eth1 (169.254.163.205) (loopback: 0)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - * 1 lo (::1) (loopback: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - * 3 eth0 (2603:6000:9843:6e0f:211:32ff:fe8c:900) (loopback: 0)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - * 3 eth0 (fe80::211:32ff:fe8c:900%eth0) (loopback: 0)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - Creating NetworkServices singleton.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkServices: Initializing...
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Creating new service.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Got notification of changed network (first change: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Quick dispatch of network change.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Creating new service.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Got notification of changed network (first change: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Quick dispatch of network change.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Creating new service.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Got notification of changed network (first change: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Quick dispatch of network change.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Creating new service.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Got notification of changed network (first change: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Quick dispatch of network change.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Creating new service.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Got notification of changed network (first change: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Quick dispatch of network change.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Creating new service.
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Got notification of changed network (first change: 1)
Jan 12, 2021 09:03:14.653 [0x7f430035b740] DEBUG - NetworkService: Quick dispatch of network change.
Jan 12, 2021 09:03:14.654 [0x7f430035b740] DEBUG - Starting HTTP server.
Jan 12, 2021 09:03:14.654 [0x7f430035b740] DEBUG - Running server...
Jan 12, 2021 09:03:14.654 [0x7f430035b740] DEBUG - Waiting for server condition to be signaled.
Jan 12, 2021 09:03:14.654 [0x7f42f4835700] DEBUG - NAT: UPnP, found device <http://192.168.0.240:5000/ssdp/desc-DSM-eth0.xml> with private address <192.168.0.240>
Jan 12, 2021 09:03:14.654 [0x7f42f4835700] DEBUG - NAT: UPnP, not an IGD: <http://192.168.0.240:5000/ssdp/desc-DSM-eth0.xml>.
Jan 12, 2021 09:03:14.654 [0x7f42ded3b700] DEBUG - Network change for advertiser.
Jan 12, 2021 09:03:14.654 [0x7f42ded3b700] DEBUG - NetworkService: Setting up multicast listener on 0.0.0.0:32414
Jan 12, 2021 09:03:14.655 [0x7f42ded3b700] ERROR - NetworkService: Couldn't join multicast group: set_option: No such device
Jan 12, 2021 09:03:14.655 [0x7f42de471700] DEBUG - Plex Tuner Service starting.
Jan 12, 2021 09:03:14.655 [0x7f42df317700] DEBUG - NetworkInterface: Watching for changes on the interfaces.
Jan 12, 2021 09:03:14.655 [0x7f42de183700] DEBUG - HttpServer: Set up a thread pool with 2 threads.
Jan 12, 2021 09:03:14.655 [0x7f42de183700] DEBUG - Running database fix-ups.
Jan 12, 2021 09:03:14.655 [0x7f42ded3b700] ERROR - Error broadcasting message: send_to: Network is unreachable
Jan 12, 2021 09:03:14.655 [0x7f42ded3b700] DEBUG - Network change for advertiser.
Jan 12, 2021 09:03:14.670 [0x7f42f50ff700] DEBUG - Completed: [127.0.0.1:57934] 200 GET / (5 live) GZIP 9ms 1189 bytes
Jan 12, 2021 09:03:14.672 [0x7f42f53ed700] DEBUG - Completed: [127.0.0.1:57936] 200 GET / (5 live) GZIP 11ms 1189 bytes
Jan 12, 2021 09:03:14.672 [0x7f42f53ed700] DEBUG - Completed: [127.0.0.1:57938] 200 GET /servers (5 live) GZIP 10ms 491 bytes
Jan 12, 2021 09:03:14.673 [0x7f42de75f700] ERROR - Error issuing curl_easy_perform(handle): 6
Jan 12, 2021 09:03:14.673 [0x7f42de75f700] WARN - HTTP error requesting GET https://plex.tv/api/photos/profile (0, No error) (Could not resolve host: plex.tv)
Jan 12, 2021 09:03:14.673 [0x7f42de75f700] ERROR - AutoTagging: unable to retrieve updated word lists
Jan 12, 2021 09:03:14.673 [0x7f42de183700] ERROR - Error issuing curl_easy_perform(handle): 6
Jan 12, 2021 09:03:14.673 [0x7f42de183700] WARN - HTTP error requesting GET https://plex.tv/api/v2/release_channels?X-Plex-Token=xxxxxxxxxxxxxxxxxxxxd not resolve host: plex.tv)
Jan 12, 2021 09:03:14.673 [0x7f42de183700] WARN - [AutoUpdateRequestHandler] Couldn't get update channels. Trying again soon.
Jan 12, 2021 09:03:14.674 [0x7f42de183700] DEBUG - HTTP requesting GET https://plex.tv/api/v2/user/privacy?X-Plex-Token=
Jan 12, 2021 09:03:14.678 [0x7f42de183700] ERROR - Error issuing curl_easy_perform(handle): 6
Jan 12, 2021 09:03:14.678 [0x7f42de183700] WARN - HTTP error requesting GET https://plex.tv/api/v
- PMS sees the IP address of the Synology (192.168.0.240)
- It cannot get out to the internet (notice the
Detected primary interface: 0.0.0.0)
My suggestion to you - Use DHCP (router assigned IP addresses) until you sort this out.
Do this for the Mac and the Synology. Restart both after making the change.
192.168.0.x and 192.168.1.x are both “Private Networks” . Changing “1” to “0” was moot.