Azure RDP boxes + Win 7

[Project2501]

Ave,

 

Doing a reach out here for assistance as I'm stuck (As are MS's TekExperts / Azure Support team).

 

I operate an Azure sub with around 20 remote desktop VM's and an RDS/CB gateway (all Server 2019). About a fortnight ago (Tuesday 8th // Wednesday 9th) my clients with Windows 7 workstations stopped being able to connect in to the platform. Windows 10 workstations weren't affected.

 

Naturally I did the things you'd usually do, but here's the rub. I do my patching over the weekend, so the morning of Wednesday 9th when the problems are being reported in, none of my VM's have had the previous days updates or been restarted - yet the problem exists.

 

So I log it with Azure, and have a few days of going around the houses with both them and my clients; and it gets stranger still. MS and myself both spin up a Windows 7 box, nice and fresh, and can get connected in without issue. We both deploy the full rack of updates, still no problems getting connected in.

 

Which leaves me with about a dozen or so users, across multiple companies, infrastructures, patch cycles and endpoint protection suites with the only point of obvious commonality being Windows 7 and all unable to connect.

 

I've got extracts of updates from problem systems, I've got wireshark dumps as well - none of it so far has shed any light on the problem at all.

 

I'm open to suggestions!