SLL Webhosting, Plex & Port 443

So I’m working on deploying HTTPS webhosting now on my network, and when I port forward Port 443 to my Windows IIS Server, Plex service gets wrekt and stops working securely, and ultimately becomes unreachable outside of my network. How can I fix this? Do I need to reverse proxy a specific url or host? Also, secure connections have not been working in my network since I implemented a custom DNS server (Windows Server 2012r2), but I did get Plex working insecurely locally by a help article on plex.tv. Does anyone have any experience with this? What am I missing?

Plex is already using secure connections out of the box. Just don’t mess with the communication yourself.
And don’t ever reroute traffic or try to put plex web into your own portal page or your own domain or browser frame as this will break things.

Just make sure that your DNS server has an excemption defined in its configuration to allow ‘DNS rebinding’ for subdomains of the domain *.plex.direct
Only then, the plex crypto certificate stays valid, as it uses ‘certificate pinning’.

Read more here: https://support.plex.tv/hc/en-us/articles/206225077-How-to-Use-Secure-Server-Connections

Ok, but the issue is I need to move my websites to https, and share the 443 port thus putting Plex behind a reverse proxy. So what URL does plex try and reach over https (443)?

Plex is not a website (not a normal one at least).
It uses port 32400 on the LAN, both for http and for https.
Which port you expose on the WAN side of your router is your choice.
Just define any portforwarding and put the external port number in Plex’s preferences. (Settings - Server - Remote Access - ‘Manually specify port’)
The rest is handled by Plex.