SOLUTION: Conversion failed. The transcoder exited due to an error

These are all new updates. It is possible that a change here November 13, 2018—KB4467708 (OS Build 17763.134) - Microsoft Support or the previous update November 13, 2018—KB4464455 (OS Build 17763.107) - Microsoft Support introduced the problem

Last time this happened a week later Microsoft issued a fix

We can try and get some diagnostics for this error. The error manifests itself with the following text in the Plex Media Server.log just before the transcoder process fails and exits
ERROR - [Transcoder] av_interleaved_write_frame(): Unknown error
and
ERROR - [Transcoder] Error writing trailer of media-%05d.ts: Invalid argument

Assuming you are still getting these errors, we need to capture loopback packets at the time of such errors

There is a good and easy to use command line tool RawCap available here RawCap - A raw socket sniffer for Windows

Download it and then start an elevated command line window (Start / run / cmd and right click and select Run As Administrator)
Then cd to the directory where you placed RawCap.exe
and run it
It will list the network interfaces
Enter the number for the 127.0.0.1 interface
Then confirm the output filename when prompted

So now it is capturing 127.0.0.1 traffic to that file

Reproduce the problem
Capture the server logs
and stop the RawCap capture by breaking in on it with control and c
Upload the Plex Media Server logs zip and send me by Private Message zip of the Rawcap pcap file produced