Installing/Running Plex in VMware

Hi!
So a couple weeks ago I noticed my meta data wasn’t being downloaded and processed. So in trying to figure out why, I discovered that my plex server was out of date. Except, apparently now Win7 isn’t supported. I planned to just live with it till I can find time to update the who system, but a couple days ago all players stopped being able to access the server. I can bring up the web app of the server remotely, but it only shows me non-local content.

I dont have a ton of time to mess around with it, but wanted to get something back up and running quick, and ideally, remotely while I have free time during my lunchbreak.

Because setting up a whole system and transferring drives is long process as I setup the server in a very hard to reach section of my basement, I went down this path: I installed Win10 in a VM, share and mount folders to drive letter. The idea here is I can just share the folders to VM and get back up and running.

However, I goto the Plex download page, but…it cant determine the operating system. So 1. Is that normal with VMs? I then goto another Win10 pc and download the installer, transfer it and install. Seems to go fine, but then, when I goto the web app(ip:port), it get’s stuck on “Getting Started” and constantly refreshing (even when left for 24 hours). Never shows anything as far as setting up the server. I can goto the ip:port/web and it’ll show me the non-local stuff, but when it comes to setting up the server it literally tells me “get plex media server”

I had also tried this with a ubuntu VM had had very much the same result. Just wondering if I’m doing something wrong here?

I’m aware running through a VM is…less than ideal, but I was expecting a fairly simple setup and was actually surprised it didn’t just go without a hitch.

A) Use windows 11 VM, windows 10 is end of life in a couple months.
B) never rely on OS detection for selecting the correct software. Here is a link to the current windows x64 installer

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