Hello Chris,
This behavior is the usual nonsense from Microsoft and it has been a problem for the last 10+ years.
i.e. Some updates on particular systems will not install and they roll back during the reboot. Contact MS support and they go through their standard process of blaming you and wasting your time with all of the usual steps until you give up and go away. I've been doing Windows Server support for over 30 years, and I can tell you that they are experts at this support methodology.
It has been my experience that sometimes a future Windows CU may install successfully in which case you will eventually get the July 2026 fixes, but that is not a good solution for a production system.
I had one particular server in a lab environment that would only take the latest monthly CU once every few months, but it eventually stopped taking any CUs. The only solution was to retire that (physical) server.
I posted this because A) I have a server that has never had any issues until now - KB5099538 keeps rolling back. B) You are not the only person reporting issues with the July 2026 CU C) Others may be wasting time with MS support refusing to examine the root issue with a CU but instead looking for ways to blame your server. Your server may have never had any issue before but as of the July 2026 CU the server has magically become "corrupted" as Microsoft likes to assert.