PMS failing to start after updating from 1.18.1.1973 to 1.18.3.2111

Server Version#: 1.18.3.2111
Player Version#:
Windows server 2012R2

The update process reports a success in the logs, but when PMS tries to start back up it pops up a window on the server that just says Error with an OK button. No additional log output is written.
Windows event logs have no additional information, only that the msi install happened.
I’ve attempted this multiple times, including enabling verbose logging and trying it again, however once the install finishes and PMS starts up, again, it writes nothing else to the logs and just says Error in the Windows UI.

This is a VM so I revert the snapshot and all is good.

The last entry from the logs, is the Plex update Service Launcher that looks like this:
Dec 05, 2019 07:39:42.885 [3400] INFO - Plex Update Service Launcher v1.18.1.1973-0f4abfbcc - Microsoft PC x64 - build: windows-x86
Dec 05, 2019 07:39:42.885 [3400] INFO - Windows version: 6.2 (Build 9200), language en-US
Dec 05, 2019 07:39:42.885 [3400] INFO - 8 2394 MHz processor(s): Architecture=0, Level=6, Revision=11266 Processor Identifier=Intel64 Family 6 Model 44 Stepping 2, GenuineIntel
Dec 05, 2019 07:42:05.124 [2472] ERROR - Bundle Exit Code: 0 - The operation completed successfully.

I’m super stumped if anyone has an idea.

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