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We had launched a windows server 2016 in a VM hosted environment, applied both CIS Benchmark for windows server 2016 level 1 and CIS benchmark for IIS 10 level 1.

At this point all of the three computers can RDP to it.

But after rebooting the server, two windows 7 laptops could not RDP to the server. We are able to see the "Enter your credentials" window, but after entering password and hit enter, it says

enter image description here

Interestingly, one windows 10 laptop can RDP.

We are in the same local network, using the same public IP, which is whitelisted by the server's firewall. The two computers that cannot RDP have windows 7, the one that can has windows 10.

  • 2
    Are all of your systems completely up to date with Windows updates? There were several patches that broke RDP over the last few months. – sippybear Oct 5 '18 at 20:31
  • Have you checked if it is registry settings for the CredSSP vuln? – birdwes Oct 5 '18 at 22:51
5

This Windows update may be missing from your Windows 7 systems. It adds TLS1.1 and TLS1.2 support to Windows 7 and Windows Server 2008 R2 systems.

It's KB3080079 just in case the link dies.

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