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RDP issues, remote computers requires network level authentication

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Hi,

First of all, please note this: 

  • Network level authentication IS supported on all machines as per theAbout Remote Desktop Connection. So please don't ask me to check this on the about remote desktop connection window.
  • All clients are set per GPO to use the Remote Setting of the "more secure" option:
  • The problem is on random machines, all windows 7. We only have a few windows 10 machines but no issues found on those so far. 
  • It doesn't matter if the RDP connection is initiated from a windows 7, windows 10 or Windows Server 2012 R2. The problem remains and is exactly the same.
  • The problem exists when attempting to connect RDP from personal home PCs (not managed by company GPOs and MS update schedules) over VPN

So the problem is this, first comes the first message and then the second.

It seems to have started after we deployed some Microsoft server updates, but its very inconsistent, some sites seems worse off then others, but its not all machines at any site. We haven't even done client updates yet.

Again, please don't give me a link to an old post or blog saying that I need to enable network level authentication, as shown by the top screenshot, it is already enabled/supported.

I already spent hours googling this. Please, I want responses from people who have actually had the exact same symptoms and issues or someone who has an idea that I haven't already clearly stated that I've checked above already.

Thank you.


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