Have you ever wondered why your Remote Desktop Connection on your Mac works well on one system but not on another?

I was testing out my connectivity to some of my customers’ network using Remote Desktop Connection on my MacBook Pro. This used to work on one of their environments but now it doesn’t. I was under the impression that there must be something that changed on my system. So I did a quick check but couldn’t find anything that has changed on my MacBook Pro (it simply means that I rely so much on VMs that my host machines – whether PC or Macs – don’t get changed that often.) What’s even more frustrating is that it works on one environment but not on another. This clearly means that there must be something that was changed on my customer’s environment.

After asking a bunch of questions, it appears that they have upgraded their server operating system from Windows Server 2003 to Windows Server 2008 R2. Since Windows Server 2008 R2 is secure by default, some of the security policies in place may be preventing the Remote Desktop Connection for Mac client from establishing a connection. But here’s where my confusion lies. The error message does not tell me anything related to those security policies.

You were disconnected from the Windows-based computer because of problems during the licensing protocol.

I mean, seriously, how does that error message help me? The reason I ask is because I have configured a Windows Server 2008 R2 Terminal Services server in the past and I was able to connect from a MacBook using the Remote Desktop Connection for Mac client. Because I cannot do anything on the server to fix this issue, I decided to dig deeper (a.k.a do a Google search.) It seems that there are a lot of people who are experiencing this same issue. A very popular forum post regarding this issue is from Microsoft TechNet where the thread kept going for more than a year. Somebody pointed out a Microsoft KB article that outlines the steps that you need to do on the Terminal Server. As I mentioned, this is not the path that I can take unless I’m the server administrator. One thing did work for me: v2.1.2 of the Microsoft Remote Desktop Connection for Mac. I have searched for it on the Microsoft Download Center but could not find it anywhere. Technically, this is still an unsupported product so be aware that you might not get any help from Microsoft when using this. Install it on your Mac, run it and test your connectivity to a Windows Server 2008 (or higher) Terminal Server.

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