Sysprepped server not automatically AzureAD joined
Around the start of the corona crisis a client of ours needed a big upgrade for his RDS farm. The current farm existed of 5 RD servers and 1 gateway. We would sysprep 5 servers for a total of 10 RD servers.
I should mention that those RD Servers are hybrid joined, local and via AzureAD. We configured the 5 servers en went about our day. Until users started complaining about conditional access policies on the RD servers. Five of them were not AzureAD joined and that caused problems.
Manually running the workplace join task (Task scheduler>Microsoft>Windows>Workplace Join>Automatic Device Join) dit not help, it just created these errors. After a long internet search i found the solution.