Solved this problem by installing Tailscale on my Opnsense firewall and making it as the exit node. Then created a NAT rule for port forwarding Plex ports.
Probably not the solution which people would have hoped for, esp. if they don’t run firewalls, but this was the way to go. Used this video : https://www.youtube.com/watch?v=VD2oMin_V3M and combination of ChatGPT to get it going. I was not getting the setting to show up on the firewall GUI(unrelated topic)
sunen3,
Thank you for the post but your suggestion is beyond my technical skills. For now I’ve bounced back to the Synology NAS with Tailscale installed and remote access is working same as before albeit laggy due to the Ryzen R1600 processor.
The latest plexamp update broke access AGAIN!! 
No, it didn’t. There were no changes to that part of the app at all. Instead of making things up, post some logs and we can see what’s going on.
Reinstalling was the only way to go and that shouldn’t be the case.
Sounds like an Android issue, you should never need to reinstall. Either that or Google chromecast library issue.
This is only on iOS devices. Android devices have no problem connecting.
It works fine on my iPhone and iPad.
I was able to identify an issue with Tailscale support that affects users on T-Mobile. Tailscale cannot tunnel properly if the iOS device is on T-Mobile and uses 464XLAT. The workaround is to use IPv6 or use a different VPN solution. Tailscale is aware of the issue and is attempting to find a resolution…
wingcomm, I have T-Mobile, I have remote access on my IOS phone to all Plex media via Windows 11 but not music. Where does Tailscale fit in with selectively unable to tunnel music? Music only? or is this still a Plex issue?
I’m off Widows 11 at this time and back on the DS923+ and have full remote access to all Plex media (albeit less responsive than a PC).
There seems to be an issue that exists based on how the App accesses network resources. Some apps work fine with Tailscale and some don’t an the packets get sent out via 464XLAT instead of being captured by the Tailscale tunnel. You can test this by trying a few differing ping apps and you’ll see that some apps try to ping a IPv6 address instead of the tailnet address while others tunnel it fine. I am only aware of it on iOS/iPadOS devices using a T-Mobile data connection (not MVNOs such as Mint). It used to be an issue on macOS devices tethered to T-Mobile hotspots but that appears to have been inadvertently fixed.
I had this problem and then enabled subnet routing on tailscale and it was fixed. You may also need to enable Custom server access URLs and also define LAN Networks in PMS Network settings, e.g. 192.168.1.0/24.
It’s definitely some combination of iOS and T-Mobile. My situation is similar. I have T-Mobile Home internet for server (So CGNAT) and use Twingate to tunnel. On my T-Mobile Android device with Twingate, plexamp and plex app work flawlessly. On my T-Mobile iPhone, the plex app will work with Twingate but the plexamp app will only work on wifi, not T-Mobile cellular. I’m not a network guy (although I do work for T-Mobile if anyone at Plex wants me to try and get something in front of anyone), but based on previous comments I think it has to do with how the plexamp app accesses the internet. Instead of forcing its way using the VPN wireguards it tries for cellular. Which means plex thinks it isn’t local which kills it.
stop thinking and start posting logs so we can help 
iPhone WiFi with Twingate Plexamp-Logs-2025-02-21-2.zip (128.1 KB)
iPhone Cellular with Twingate Plexamp-Logs-2025-02-21-1.zip (107.2 KB)
Android plex tmo cellular.zip (468.8 KB)
Attached (hopefully I captured them correctly) are as follows:
All have server behind T-Mobile ISP (windows 11).
Both phones utilize Twingate VPN due to CGNat
One log is android on T-Mobile cellular with TG, plexamp good to go.
One log iPhone on T-Mobile cellular with TG, no joy (only cahced songs will play, artist will not load, server says oops try again)
Third log is iPhone on wifi (non-local wifi, different than server, believe it’s xfinity) with TG, plexamp working fine with artists and music loading.
IPhone and plexamp latest builds, android latest updates.
Hope this helps identify something. Let me know if I did it wrong ha.
thank you! traveling but will check out as soon as i can.
These are the two URLs it’s trying to use, and neither of them work.
Feb 21, 2025 14:54:54.881 [Javascript] WARNING - DEVICE: Server connection https://192-168-86-21.2dc9b6a334254b0db8c1f15ed32c59b9.plex.direct:32400 didn't work for LittleBee: HTTP status -28
Feb 21, 2025 14:54:54.888 [Javascript] WARNING - DEVICE: Server connection https://172-58-123-26.2dc9b6a334254b0db8c1f15ed32c59b9.plex.direct:18539 didn't work for LittleBee: HTTP status -28
I’m assuming those were from the iPhone log? I guess the questions would be why do they work on non-local wifi with the VPN but not with the cellular w/VPN. Again, my thought was that the iOS app for amp is trying to connect via celluar ip first instead of the vpn.
It uses all addresses it sees as being available, and whichever one works and is fastest is used.
I’m not sure how you’ve configured your VPN and what IP you expect it to using. You can post the log from the Plex app and I can see what address it’s using (try playing something first).
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