Plex Unreachable with Synology NAS (Reverse Proxy Issue?)

I’ve been researching this issue for about a week and no forum post on any site has been able to explain this clearly so I’m trying here.

I’ve set up a fully functional Plex server on a Synology NAS at home. Because it works great and has offline capabilities I decided to set up another internal NAS/Plex server on the ship I am on. As a whole it works great and I have no issues. The majority of the time it is disconnected from the internet and about once a month I connect it to refresh the metadata of any new stuff added. In an attempt to improve the network I decided I wanted to make it easier to access. Instead of everyone typing in the ip address “192.168.1.142:32400/web” I wanted to make it simply “plex.mydomain.com”.

In my attempt to do so I learned about Synology’s internal DNS server. After more research I realized since plex and the nas are on the same ip address but on different ports that this is not a viable option. (Unless you can change Plex’s internal IP address somehow?)

I then learned about a reverse proxy. Synology has one built in (that I believe is nginx? not really 100% sure on this). This is supposed to redirect an address typed in the url to a specific ip address & port. This worked! Sort of… now whenever I type in “plex.mydomain.com” Plex will pop up but it says that the server is unreachable. Typing in the actual ip address plus “:32400/web” still works though. Why is this? Is there a setting I’m missing? Is this a Plex issue or a Synology issue? I’m still learning about DNS and reverse proxying and I’m not sure why this has happened.

This network is entirely offline/internal so port forwarding or any of the other tricks won’t work. I’ve tried a couple other settings but this was the closest I got to it working. Is it even possible to set this up like I want it? Or is there a better way to do it than I am trying? Thanks in advance.

Settings:
issue2

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