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Issue with Console Session vs RDP sessions

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Hello, 

I have a Server 2008 R2 with 10 Remote Desktop User CALs that I have been confirmed to have licensed properly, several times. My issue is that occasionally when some users connect they see the message that there are too many people logged in and they need to choose someone to kick off. This makes no sense to me as every time it has happened, I have logged in to see that there were 6 people logged on. There is noting weird in the event log besides a flood of schannel alerts and incorrect passwords. 

Here are my current theories.

  1. Most of the users who use remote desktop, use the remote desktop app on their MacBooks, perhaps there is a licensing conflict with Mac vs windows?
  2. The previous IT guy setup a publicly available host name that translates to our static IP that allows RDP traffic through to our terminal server. Regardless of if you are inside or outside of the network you can RDP to the host name and gain RDP access. I am in the process of restricting access to only go through a VPN but could there be some issue there in terms of lingering connections?
  3. I have setup the domain policy so that any user is automatically logged off after and hour of idle time and the session locks after 15 mins of idle time and I have required that all RDP session use whatever form of RDP encryption they are capapble of. Could these Policy restrictions be causing the issue?
  4. I am open to other theories.

I have attached a sample image of the issue and can send a redacted version of the GPresult report. I would love to see if you guys can help me out.


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