Server can't connect to plex.tv, remote access stops working

Plex Media Server Remote Access
1

Server Version#: 1.25.2.5319
Player Version#: all players (Web, Android TV, Android phone)

I’m having a weird issue with remote access that has occurred twice in the past week, and a couple more times a longer while ago. The server is not accessible outside the network, even if the dashboard says it is. Restarting the server will make the dashboard update and show Unknown for both the private and public IPs. Port is forwarded in the router, I’m not behind double NAT, and everything has been working fine for years until recently.

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Moreover, I have a script on my server that downloads the latest update from plex.tv via wget and it always hangs when this problem manifests:

wget https://plex.tv/downloads/latest/...
Connecting to plex.tv (plex.tv)|52.48.253.46|:443... connected.
# hangs indefinitely

The problem always solves itself in a couple of days, but there’s nothing I can do to expedite the process. I tried restarting the Plex service, rebooting the server, rebooting the router, changing the public port, nothing works.

I can DM server logs to an admin, here’s a snippet from them:

Dec 20, 2021 12:58:38.697 [0x7f60d0f0cb38] ERROR - Error issuing curl_easy_perform(handle): 28
Dec 20, 2021 12:58:38.697 [0x7f60d0f0cb38] DEBUG - HTTP simulating 408 after curl timeout
Dec 20, 2021 12:58:38.698 [0x7f60d0f0cb38] ERROR - HTTP 408 downloading url https://plex.tv/updater/products/5/check.xml?build=linux-x86_64&channel=8&distribution=debian&version=1.25.2.5319-c43dc0277
Dec 20, 2021 12:58:38.698 [0x7f60d0f0cb38] INFO - AutoUpdate: error getting data from plex.tv
2

So I’ve been having this problem for the past 24 hours, rebooted the server and it didn’t work. Rebooted the router just now and the server is once again accessible remotely. Last time this happened a router reboot didn’t immediately work, and the problem “fixed itself” a day later. I don’t know what’s happening, I’m glad it’s fixed now, but would be nice if I can get to the bottom of this…

3

Happened again, finally called the ISP, they reconfigured their equipment, I restarted my router, problem solved.

For people having similar problems, I’m writing all the troubleshooting steps I took to diagnose this (to no avail really…)

❯ curl -v https://plex.tv                                                                                                                                                                                            
* Rebuilt URL to: https://plex.tv/                                                                                                                                                                                   
*   Trying 54.75.185.8...                                                                                                                                                                                            
* Connected to plex.tv (54.75.185.8) port 443 (#0)                                                                                                                                                                   
* found 129 certificates in /etc/ssl/certs/ca-certificates.crt                                                                                                                                                       
* found 516 certificates in /etc/ssl/certs                                                                                                                                                                           
* ALPN, offering http/1.1                                                                                                                                                                                            
* gnutls_handshake() failed: Error in the pull function.                                                                                                                                                             
* Closing connection 0                                                                                                                                                                                               
curl: (35) gnutls_handshake() failed: Error in the pull function.  

> openssl s_client -connect plex.tv:443 

140234092029592:error:14077438:SSL routines:SSL23_GET_SERVER_HELLO:tlsv1 alert internal error:s23_clnt.c:769: 
CONNECTED(00000003)
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 7 bytes and written 265 bytes
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
    Protocol  : TLSv1.2
    Cipher    : 0000
    Session-ID: 
    Session-ID-ctx: 
    Master-Key: 
    Key-Arg   : None
    PSK identity: None
    PSK identity hint: None
    SRP username: None
    Start Time: 1641245573
    Timeout   : 300 (sec)
    Verify return code: 0 (ok)
---

My router is a Linksys EA8350, connecting through PPoE to my ISP’s modem in bridge mode. Port forwarding is configured correctly, setup ran fine for 3 years, problem started manifesting in the last month every ~10 days.

When the problem happens it’s not just plex.tv that my server has trouble connecting though, some other HTTPS sites don’t work either, and curl and openssl produce the results above.

The funny thing is that if I connect remotely to my server through VPN running on it, than all the HTTP sites work. Moreover, I can directly connect to my Plex server through the local LAN. Connecting to my WAN IP and forwarded port also works fine.

Anywho, everything is back up and running now, thanks if you read so far, may the ISP and Plex gods shine upon you.

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