Plex Media Server works remotely on the Plex Android app, but not browser - unable to connect to "speedy" securely

Server Version#: Version 1.26.0.5715
Player Version#: Version 4.81.1

Plex Media Server is running fine locally. I can watch movies from my Fire Stick. I can also connect over Mobile Data with my Android phone and using the Plex Android app. I don’t have a Plex Pass so I only get 1 minute of video, but it does work.

But when I use app.plex.tv in a browser and try to connect remotely, I get the error that app.plex.tv is unable to connect to “speedy” securely. Speedy is the name of the computer my Plex Server is running on - Windows 10. Why can I connect remotely using the Plex Android app (on phone using mobile data), but not remotely using a web browser on a Windows or MAC computer? This used to work OK in the past with the web browser. I’ve tried a few web browsers and get the same results.

Obviously, in Plex settings, the remote access has a green check mark. I’ve forwarded the port correctly because it works with the Android app.

I have Plex behind an Untangle Firewall that uses SSL inspection, but I’ve tried it with all the security features of the firewall turned off and there is no difference - still get the same message. I’ve seen where some people toggle the “required” and “Preferred” secure connections options in the server settings and that gets it working, but it didn’t for me. I’ve also logged out and back in both the server and web with no help. I’m stuck.

Any ideas how I can get this working again? It used to work just fine, even with the Untangle Firewall in place. I’m not sure what changed.

In case it matters, the only “wrong” thing I see in the Plex setup is that in the “General Settings” of the server in the update section, I see this: Version 1.26.0.5715 Something went wrong. Please install manually..

That’s interesting. Share a diagram and the relevant configuration?

If your Plex server’s OUTBOUND connections to the Plex cloud are impacted, it’s possible Plex can’t get & install its own server certificates. Share server logs.

Thanks for the response, @Volts. What’s throwing me off (though I will freely admit that I’m a Plex USER and don’t understand the behind-the-scenes of how it works) - is that this used to work OK. And still does using the Android App.

How should I upload my logs? There are a lot of them. Maybe just the “Plex Media Server” file? I suspect there might be some info in it I don’t want to share, right? (username/password/IP address).

Here is a link to a network diagram.

There are some entries mentioning certificates…

For the Windows firewall on the PC running Plex Media Server, I have “Firewall & network protection” turned off. I also have “Tamper protection” turned off in the Virus & threat protection settings. I also have the free version of Malwarebytes running, though I don’t think that has any real-time protection since it’s the free version.

Here is the Plex Media Server logs with my personal info changed (I hope I changed all of it).
redacted-Plex Media Server.log.txt (4.3 MB)

May 11, 2022 23:05:33.041 [13680] WARN - [HttpClient] HTTP error requesting GET https://plex.tv/media/providers?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (60, SSL peer certificate or SSH remote key was not OK) (SSL certificate problem: unable to get local issuer certificate)

Plex can’t communicate with the Plex cloud. Stop performing interception on the Plex server’s outbound traffic.

Alternatively, add your local CA cert to Plex’s trusted store. Look for a cacert.pem file in the Plex Resources directory.

May 11, 2022 23:05:55.967 [9852] ERROR - getaddrinfo(192-168-2-101.abcdefghijklmnopqrstuvwxyz012345.plex.direct) failed: 11001

Also disable DNS rebinding blocking for *.plex.direct. I imagine the kitchen-sink firewall is doing this too.

I added the Untangle certificate that it uses to intercept SSL traffic to the Plex file you mentioned.

I’m using a Pi-Hole locally for DNS. Don’t have DNS set up in the firewall, except to point DHCP clients to the Pi-Hole for DNS. But honestly, I’m lost on how to even check for DNS rebinding anywhere else.

I currently have all the apps disabled in Untangle now, so they should not be interfering with any inbound or outbound traffic.

I’m not an expert in my Untangle firewall either, so I may have to go to their forums for assistance.

From my firewall troubleshooting section, I can’t ping plex.tv (but suspect they’re blocking Pings) but I can do a “Connection Test”. Plex.tv is reachable from my home network:


Thu May 12 2022 13:14:26 GMT-0500 (Central Daylight Time) - Test Started
Test Successful
DNS fwd/rev mismatch: plex.tv != ec2-52-49-172-158.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-18-200-219-245.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-52-209-234-37.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-63-34-174-176.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-54-171-30-185.eu-west-1.compute.amazonaws.com
plex.tv [52.49.172.158] 80 (http) open
Thu May 12 2022 13:14:28 GMT-0500 (Central Daylight Time) - Test Completed


Thu May 12 2022 13:14:33 GMT-0500 (Central Daylight Time) - Test Started
DNS fwd/rev mismatch: plex.tv != ec2-54-171-30-185.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-63-34-174-176.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-52-209-234-37.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-18-200-219-245.eu-west-1.compute.amazonaws.com
DNS fwd/rev mismatch: plex.tv != ec2-52-49-172-158.eu-west-1.compute.amazonaws.com
Test Successful
plex.tv [54.171.30.185] 443 (https) open
Thu May 12 2022 13:14:35 GMT-0500 (Central Daylight Time) - Test Completed


But is it odd that from my firewall, a traceroute is going to 52.49.172.158 and when I do a tracert from Windows (which doesn’t make it all the way), it’s going to 63.34.174.176. The trace dies after the last hop seen at twelve99-cust.net network (80.239.195.91).

A traceroute from my firewall ends up at 24 ec2-52-209-234-37.eu-west-1.compute.amazonaws.com (52.209.234.37) 116.914 ms 119.703 ms 116.257 ms
Test Successful

Now, my Android Plex app no longer works over the Internet. It will only work if I connect to home via OpenVPN.

I’ll review your suggestions @Volts and see if I can get through this.

As what I thought might be an alternate test to see if my Plex Media Server can connect to plex.tv for remote access, I removed the manual port-forward in my Untangle Firewall. Then I turned on UPnP in the Firewall. I changed the config in Plex from specifying the port and letting UPnP set it up.

There’s a green check by the Remote Access in Plex again.

Then I went into my firewall and see that it dynamically created a port-forward. So my Plex Media Server appears to be able to reach plex.tv and set things up.

But I still get the error about being unable to connect securely.

I’ll still re-visit your suggestions @Volts – work is getting in the way.

I have it working on the Android App remotely now - some progress. But I think it’s still broken through a web browser at app.plex.tv.

In my firewall SSL Inspection, I turned off TLS v1.3 inspection. After that, the Android App is working.

Still trying to get the browser to work through the Internet.

I think I have it working now.
None of the things above seemed to do the trick, except maybe using UPnP instead of a port-forward, but I doubt it was that also.

I logged out of the Plex Server and back in and it started working. Well, my daughter needs to verify, but it’s working for me.

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Nice!

It’s possible a few things were necessary. Plex may not have been able to log into the cloud correctly until the SSL issues were resolved.

Or maybe it was none of that. :wink:

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