GlobalShop EPR, that thing is written in cobol ffs. You can virtualize it, but only on ESXi - like this matter at all, but that's what they support, it runs on PervasiveSQL. So basically one big wtf.
Autodesk Vault, you're tied up to MSSQL, no cloud equivalent, no plans to support other databases. They also force you to run built-in backup tool, so your existing VM level backup system, like Veeam, has to backup twice as much data. Other Autodesk software is not much better.
Mastercam, they force you to use USB dongle for licensing, and using USB boxes over ethernet is unsupported. It might work but you won't be able to update the licenses on the dongle. So say hello to physical Windows box in your server room.
Other than that almost any ERP system that runs strictly on Windows. They will do anything so you run it on physical box, and if client runs in web browser, it will be Internet Explorer only, god forbid if it's newer than version 8. Ideally you should run Windows XP with IE 6.
I also have some quality control equipment from Pratt & Whitney, software runs on 32bit Windows 7 only. So I have one zombie PC.
I feel any software that touches manufacturing sector will be like that, stuck in the past.