App.plex.tv unable to connect securely

Plex Media Server NAS & Devices
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1

Server Version#: 1.29.2.6364-7000
Player Version#: 4.87.2
<If providing server logs please do NOT turn on verbose logging, only debug logging should be enabled>

Hello, everyone. Apologies in advance as I do not think I am dangerous enough to be called a technical user and, secondly, even though I have looked, in case this issue has been resolved before. I have a Synology DS923+ running DSM 7.2.1-69057 Update 3 as well as the PMS mentioned above.

My issue is that I used to be able to see my libraries from outside my local network but now I can’t! My test is using my phone which, when connected to Wi-Fi, shows me my media both in the Plex Android app as well as through the Chrome browser. However, when only using data, I get the message “app.plex.tv is unable to connect to ‘MySynology’ securely” in the Chrome browser (Plex Android app simply shows the server as OFFLINE). I had also shared my library with a friend and they used to be able to see my media as well but now can’t and get the same “unable to connect securely” message.

One of the main things that changed for me from when this worked to now was my ISP. Both ISPs provided me with their modem as I have my own router. I looked into the DNS rebinding for the current ISP (per friend’s suggestion) but they let me know they do not do DNS rebinding.

I had also tried uninstalling PMS and reinstalling it to no avail and, while I am able to see my media outside my local network if I enable remote access, I would first like to understand why I am not able to access it like before.

I am at a loss after multiple hours of research and trying different things (DSM was updated since first setting up PMS but I got this Synology only three months ago). Any help is appreciated. Thank you very much!

2

Hello, Mr. @ChuckPa. I understand you are a great helping hand in these matters. Could I request your advice to see what I can try to resolve this if possible? Thank you very much.

3

@marianomarks

Plex.tv saw your server about 2 hours ago

It’s LAN IP was 192.168.2.174

Is this what you expect?

If so, when you open http://192.168.2.174:32400/web , what happens ?

It might be the server is signed out of your account but still talking to Plex.tv
We can easily fix that if it’s the problem.

4

Yes, LAN IP is 192.168.2.174.

When I open http://192.168.2.174:32400/web while at home, I am able to see the media that I placed in the Synology. However, it does tell me that the connection to the site is ‘Not secure’. I hope that answers your questions. Thank you.

5

I need to see your server logs.

I’m not sure if the server is having trouble talking to the router & plex.tv or not.
It seems that it is.

Stop Plex
Open FileStation
Navigate to PlexMediaServer/AppData/Plex Media Server
Right-click Logs → Compress to Logs.zip
When the ZIP is complete, download it to your computer

Upload that ZIP here with your next reply and I’ll look at it.

6

Hello. Please find attached my logs. Thank you again for your help.

Logs.zip (745.6 KB)

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@marianomarks

Thank you for the logs. The problem was immediately obvious

  • DNS Lookup Failure - “Can’t resolve hostname”
Jan 12, 2024 21:06:02.643 [0x7f827c8e7b38] WARN - [HttpClient/HCl#15] HTTP error requesting GET https://plex.tv/api/v2/user/privacy?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (6, Couldn't resolve host name) (Could not resolve host: plex.tv)
Jan 12, 2024 21:06:02.643 [0x7f827b21cb38] DEBUG - [Analytics] Using cached data for privacy preferences
Jan 12, 2024 21:06:02.644 [0x7f827b21cb38] DEBUG - [HCl#1d] HTTP requesting GET https://plex.tv/api/v2/release_channels?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
Jan 12, 2024 21:06:02.644 [0x7f827c8e7b38] WARN - [HttpClient/HCl#16] HTTP error requesting GET https://plex.tv/api/v2/server/webhooks?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (6, Couldn't resolve host name) (Could not resolve host: plex.tv)
Jan 12, 2024 21:06:02.652 [0x7f827c8e7b38] WARN - [HttpClient/HCl#17] HTTP error requesting GET https://plex.tv/api/v2/release_channels?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (6, Couldn't resolve host name) (Could not resolve host: plex.tv)
Jan 12, 2024 21:06:02.653 [0x7f8281c300d0] DEBUG - [AutoUpdateRequestHandler] Using cached data for update channels
Jan 12, 2024 21:06:02.653 [0x7f8281c300d0] DEBUG - [HCl#1e] HTTP requesting GET https://plex.tv/api/v2/features?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx
Jan 12, 2024 21:06:04.334 [0x7f827c8e7b38] WARN - [HttpClient/HCl#18] HTTP error requesting GET https://plex.tv/media/providers?X-Plex-Token=xxxxxxxxxxxxxxxxxxxx (6, Couldn't resolve host name) (Could not resolve host: plex.tv)
Jan 12, 2024 21:06:04.334 [0x7f827b42fb38] ERROR - [MediaProviderManager] Error parsing content.

On the Syno, Control Panel - Network - Look at the DNS setting.

  1. If it’s automatic, then it’s pointing to your modem/router
  2. Confirm that’s the right IP address

Else

  1. You can also try setting it manually to something like google

Screenshot from 2024-01-13 17-44-17
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2. If you do change it, Restart PMS

8

Unfortunately, with either option, I still get the same results.

“Manually configure DNS server” was unchecked and the default gateway IP is what I expect. I made sure to save the settings.

I had also checked the option and set the DNS servers to Google’s DNS servers as shown in your picture, made sure to save the settings, and restarted PMS.

For restarting PMS, I only stopped the app and then ran it again in the Package Center.

As I understand it, the DNS server settings you explained are to set the DNS server that my DS923+ would use when it is making connections to the outside (i.e. the DNS Lookup Failure error)?

:+1:

9

Yes, It’s critical that your Syno be able to talk to the outside world.

DSM needs this to update itself and its apps.
If it can’t talk to the outside world, it’s going to fail (not work) eventually.

As a test, can you open Package Center, search for apps, and install them

As a test, search for and install the “Text Editor” app. It’s both useful to have, you might need it some day with Plex, and confirms the Syno can get out to the internet.

10

Hello. Yes, I have downloaded the “Text Editor” app and I am able to install apps from the Package Center.

I currently access my Syno with DDNS because I realized my photos would upload much faster than going through QuickConnect! (although I now have issues with sharing albums in Synology Photos because I got some error message involving my router’s DDNS - I wasn’t sure if that was worth mentioning).

I am open to trying more tests. Thank you for the assistance!

11

You telling me that you’re using DDNS and QuickConnect answers everything.

Plex will not accept foreign certificates (your DDNS or Synology QuickConnect) unless they’ve already been added to PMS.

That’s the catch. You can’t add them until you’ve claimed it.

For now,

  1. Ignore the DDNS
  2. Turn QuickConnect OFF.
  3. Restart DSM
  4. Now, open the Syno using HTTP://LAN.IP.of.Syno
  5. Check if Plex is running. Start if it’s not

Can you confirm for me whether or not you have an IPv4 Internet address ?
According to the forum, you do not.

The easy way to check, open http://whatsmyip.org

It should respond with XXX.xxx.XXX.xxx (4 octet IPv4 address)

If it responds with IPv6 (a whole bunch of 4 hex digit clusters), then we have a problem.

When you look at your Syno, it should have this in Control Panel - Network
(An IPv4 address). It might also have an IPv6 address.

Screenshot from 2024-01-15 18-29-45
Screenshot from 2024-01-15 18-29-45795×384 34.9 KB

When you log into your modem router, does it show IPv4 LAN address or IPv6 ?

How good are you using Putty (or ‘ssh’) command line?
Would you be comfortable doing it if I gave you the commands ?

(We can do this in PM to protect your privacy)

12

I have turned off QuickConnect and I do have an IPv4 for a public IP address.

To answer your other questions, when I look at my Syno, in Control Panel - Network, it does show my local LAN of 192.168.2.174 (no IPv6 shown).

When I log onto my router, it shows my public IP address as well as my DDNS address that I created a long time ago that ASUS provides. I see it got a Let’s Encrypt certificate for this as well which I was trying to learn more about. I wasn’t sure if this DDNS was causing trouble as well and, if it is, I have no problem turning it off as I do not really use it. I have a snapshot of this with info blurred out but I still wanted to send it via PM. I tried sending a message but it said you were not accepting messages at this time.

I haven’t used PuTTY since college :rofl: but I just downloaded it and was able to log on to the Syno with it so, if you have the commands, I am ready to try them!

13

Hello, @ChuckPa,

I was wondering if you happened to have the ssh commands I can try. Thank you for letting me know!

14

The entire process:

  1. Install the Synology “Text Editor” app.

  2. Stop PMS

  3. Using the Synology Text Editor, edit “Preferences.xml” (down in the PlexMediaServer shared folder)

  4. VERY CAREFULLY, remove the following Name="Value" full sets (Name and quoted value)
    – PlexOnlineUsername
    – PlexOnlineMail
    – PlexOnlineToken
    – PlexOnlineHome (if it exists)

  5. SAVE the file

  6. Start PMS

  7. Start PMS — Let it sit there - completely untouched

Now for the SSH part

  1. SSH into the Syno (Putty will work for this if on Windows)
  2. Go to https://plex.tv/claim
  3. NOW, within the next 4 minutes (the token expires)
  4. Go to the putty session and type:
curl -X POST 'http://127.0.0.1:32400/myplex/claim?token=PASTE_TOKEN_HERE'

It will look something like this:

curl -X POST 'http://127.0.0.1:32400/myplex/claim?token=claim-15246af3x'

  1. When you hit enter, it will sit there silently for 10-15 seconds. This is expected

  2. You’ll then get a flurry of XML in the response from Plex.tv as the new credentials are received.

  3. The server is now claimed :slight_smile:

15

Hello, @ChuckPa,

Thank you very much for the commands. After trying your steps, everything behaved as you described but, unfortunately, I still have the same issue :face_exhaling:. I am able to see the media in my local network but not outside.

I do use DDNS now to log into my Syno but, as I mentioned, my tests before were by just accessing my media with the Plex app on my phone, Plex app on my PC (using phone’s hotspot), and Plex app on a TV (that is outside my network).

I have now turned QuickConnect back on and I’ve disabled the DDNS service on my ASUS router (as I wasn’t using it at all).

Sooooo, uhh, anything else I could try…? Thanks!

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16

Hello, @ChuckPa. If you are still willing and able to give this one last stab, I wanted to ask one question. As I originally stated, when I had my previous ISP, I was able to set up Plex and see my library from different devices outside my network (TV at friend’s house and Plex app on Android using data) and I did all of this with the help of a friend who showed me I did not have to enable “Remote Access” in my Plex account settings (this is how they have it set up as well). I’m not sure how this ended up working.

I wanted to go back to this first step and ask - should that still be possible for me to do? Thanks

17

Hey, forum. I ended up turning on the remote connection function and accessing the server from the outside this way. If I ever figure out how it worked the other way, I will try to update this. Thanks!

18

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