I should start by saying that while I’m proficient in a lot of things I know just enough about networking to be dangerous. I have a relatively new problem getting my Plex server to connect to Plex.tv. This showed up when Plex moved to SSL connections using Digicert certificates in June. I also found yesterday that my daughter’s phone cannot connect to Blackberry’s OS download server and given their security focus I’m guessing it’s a similar issue. For better or worse secure banking sites continue to work although I now have a certificate mismatch with Firefox and have since moved to Chrome.
Prior to Plex’s switch to SSL in June Plex worked fine and things like Plex Sync worked as expected. Since the move to SSL in June Plex will sign in to Plex.tv intermittently - it normally takes a router reboot to connect - and almost always loses its connection after some time without being able to reconnect. Presumably Plex phones home to plex.tv every now and then, can’t get through after some time and that’s when things stop working. My router configuration hasn’t changed in a long time although I did upgrade my router to OS 6.29 around the same time the issues started. I’ve checked my DNS cache and found that plex.tv resolves to 4 different IP addresses, none of which are on a block list and each has a TTL of several days, yet Plex usually only stays connected for a couple hours. Also since June web connections to plex.tv come up as untrusted in both Chrome and Firefox (error says certificate is only valid for *.us-west-1.cloudsearch.amazonaws.com) and I can no longer ping plex.tv from my network.
Since plex.tv is pingable over my phone this looks like a firewall issue but I’m not seeing anything there that would block my connection. I’ve logged each of my firewall rules and don’t see anything getting dropped related to Plex. My assumption is that there’s an intermittent certificate mismatch somewhere and plex.tv is dropping me sometime after accepting a connection so i don’t log an error on my end. The connection to plex.tv is blocked to every device on my network (server, computers, tablets, phones) so I know this is being done at the router and not by my server itself. The router is a MikroTik RB951G-2HnD running Router OS 6.30.2 (the latest version). I’ve probably spent hours now looking at firewall settings and logs but for all I know I could be looking in the wrong place altogether. It’s also quite possible that I’ve had whatever issue is causing this for a long time and just didn’t connect to sites in whatever manner Plex now connects to their server.
Thoughts and advice from someone that knows more than I do about this stuff would be appreciated before I hose something. I’ll happily submit logs or config files, just let me know which ones.