Plex not able to connect to internet? Can't claim Plex Media Server after reinstall

Plex Media Server NAS & Devices
1

NAS: Synology DS920+
Server Version#: DSM 6.2.4-25556
Player Version#: 1.23.1.4528-6000
Plex Media Server Logs_2021-05-19_23-33-58.zip (583.1 KB)

For the past 2 days, I haven’t been able to match any of the media files, using either the new or the legacy agents. Each time I tried, it instantly came up with 0 results, despite having the TMDB-ID in the folder name. That was the first hint.

I’ve started the PMS multiple times with no success. I’ve restarted my NAS a couple of times, no luck there either. I even uninstalled and reinstalled PMS with the latest file from the website, and it doesn’t want to work still.

Now, when I try to log into my PMS via the local IP address, I have to go through the setup process, but it tells me that there is a problem claiming the server.

Every other device on my network is able to receive IP services, so why wouldn’t Plex? To better understand my network, I should list a few things, in case it turns out to be relevant.

For my router, I have an Asus RT-AX88U. FW: 3.0.0.4.386_42820. Currently, I have my router set up as the DHCP Server with a static route for the Synology NAS, and the Synology NAS acting as my DNS Server.

Why is my router using my Synology NAS as a DNS Server? Because I have PiHole installed as a container on Docker, on my NAS. I use PiHole to block ads network-wide. Even if I bypassed the PiHole completely by setting the DNS route on my router to 8.8.8.8 (Google’s Public DNS), my Plex Server still can’t connect to the internet. Not to mention it was working perfectly fine in this configuration previously.

In short: With PiHole = Doesn’t work. Without PiHole: Doesn’t work.

I also have PiHole Upstream DNS to 8.8.8.8. It’s just acting as a middleman between the DHCP and the actual DNS servers, catching most of the ads along the way. So PiHole shouldn’t the issue. The PiHole logs show’s the “plex.tv” request as green, so it’s not being blocked, just unable to resolve it for some reason.

But yeah, the IP Path of my network should be as such:

Web → Main DNS (8.8.8.8) → Modem → Router → PiHole on NAS (local DNS) → Router (DHCP Server) → End Device (Cellphone, Computer, NAS, TV, Consoles, etc)

Everything else on my network is able to get through.

I’d appreciate any and all help.

I won’t reply immediately, as it’s almost 0100 here, and I gotta get up in about 5 hours. I’ll hopefully be able to respond in about 12 hours from the time this was posted.

Edit: I would add more pictures, but I can apparently only do 2 links per post.

Update: Here is an Imgur Album with some useful screenshots of my settings mainly from my router, and a few from Synology and PiHole.

3

If I may inquire?

Does DNS otherwise resolve correctly for everything except PMS ?
( All other Synology apps & services are working )

4

I’ll be real. I seriously thought those warning messages were talking about not storing media files at that level of the folder structure, and that’s why they had the TV Series and Movie folders already there so that we store our files there instead.

Thanks for letting me know. I just moved everything into a custom shared folder at the top-level directory instead.

Mind telling me what settings I should be checking? Should I be checking the settings on my router? Settings on the Synology NAS itself? Settings in PiHole?

I got screenshots of each uploaded to Imgur, so here’s the album

6

Just my opinion but that seems like a lot of routing for a home network haha. I have always had issues with pi-hole in front of my Plex server so I just gave up. I do agree rasp pi is the way to go though if you are using pi-hole.

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@mediacenterkodi84

Do you have some information to contribute ?

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I was just stating that I too have also had issues getting Plex to work behind a pi-hole. I thought this was a contributing fact?

9

do you have any technical / addressing information you’ve observed regarding IPv4 vs IPv6 DNS resolution on Synology?

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I don’t have much else running on my Synology NAS right now, as I just built it last week. The only other stuff I got running on my NAS other than Plex is Docker, and on that is PiHole, watchtower, and Portainer.

Here’s a screenshot of some recent entries from 192.168.50.2.

11

Do you have a supervisor I can contact?

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That’s a lot of retries !

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Apologies, a 9 snuck into the url link some how. I corrected the link in the previous post, but here’s the link to the Imgur Album again.

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@mediacenterkodi84

I do if necessary. Have i offended in some way?

I am asking for information here because I’m trying to track down a DNS resolution problem with PMS builds 1.23.0 and above.

I’m working on a theory which is dependent on local host & LAN configuration versus WAN IP address.

17

I think a more professional response would have been appropriate.

Mediacenterkodi! Thank you for your input but if you do not have any new information to add. Please refrain from commenting as even though it was nice! It congests the forum post too!

Just came off as rude the way you said it and. But that’s just my perception. If you did not mean it that way. I didn’t think my info was useless. It seems you did tho. Have a nice night.

I would have just messaged that to you but your messages are turned off.

18

Thanks. I’ll be adding some more screenshots. I just normalized up my router, pointing DNS away from 192.168.50.2 and towards 8.8.8.8 and 1.1.1.1 instead. I’ll see if I can’t redo Plex in the meantime and get it working.

Confused as to what the root of the issue is though.

22

@mediacenterkodi84

If you have nothing to contribute other than harassment, I would appreciate you not posting further.

23

Thanks for the tip. I’ll reduce the DHCP range a bit right now in my router. Also, my Synology NAS has already been assigned a static IP by my router. One of the first things I did when I built the NAS with the intention of running PiHole. I use to run PiHole off a raspberry Pi, so I knew it needed a static IP. It makes sense, considering it would be functioning as a DNS. Don’t want that to change IP addresses.

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No offense, but you are cluttering up my thread with inane posts. Please stop wasting these people’s times.

I appreciate your response stating that you had issues with PiHole in front of your Plex server, but if you don’t have a fix action you yourself have done to fix it, and instead, as you said, “just gave up”, then please leave the discussion to those of us who is actually trying to fix the issue at hand.

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@cody_leo_stephens

In reviewing your logs, I’d like to ask about your internet service if I may ?

  1. Does your ISP provide both IPv4 and IPv6 ?
  2. Do you have both stacks on the inside LAN (IPv4 and IPv6 enabled in DSM) ?
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I don’t know if Cox supports IPv6. A quick google search says yes, so I would say so.

Regardless, I have IPv6 disabled on my Asus Router and no IPv6 address assigned for the gateway address on my NAS.

29

Yes. I have normalized my router, bypassing PiHole all together. I even shut PiHole down on Docker as well. With this, I’m able to claim my NAS server.

I did have to uninstall and reinstall though. It was acting pretty weird. What I mean was that before I uninstalled, I tried to claim it, but it seemed like clicking on the button didn’t do anything. I also noticed that it didn’t show my other user accounts when trying to log in, nor did it show my account in the top right corner in the drop down.

Regardless, uninstalling and reinstalling did fix it that issue.