Windows – Remote Desktop – Can’t connect to remote machine from only 1 of the 3 work machines

remote desktopwindowswindows 7

I'm having an issue connecting to a remote machine (Win Server 2012) using Remote Desktop.. but the weird thing is I only have trouble connecting from one machine that I use. I can connect from two other machines fine, even with the same credentials. From the problem machine (Windows 7), I am given a login prompt before seeing the error pictured at the end of the post. I can remote to several other servers from the problem machine without issue.

Things I've tried so far:

  1. Connecting to the remote machine using the fully qualified domain name
  2. Connecting to the remote machine using the IP address
  3. Logging in to the remote machine with the system administrator account
  4. Switching the problem machine IP to static and setting it to a known IP address from a "good" machine
  5. Deleting the default.rdp file in My Documents on the problem machine
  6. Checked everything in this help article… most of this stuff can be eliminated automatically because many other machines can connect. I did however double check Windows Firewall on both my machine and the server, as well the Network Level Auth settings on my machine.
  7. Checked the remote machine's Event Viewer logs. Nothing to be found in the log immediately after a failed connect attempt from the problem machine

Again… I can connect to this server just fine with my credentials on two other client machines (one is Windows 7, one is Windows 8.1). What am I missing here?? What else can I try to figure this out?

The error:

error image

EDIT

Group policy settings on the server:

group policies

The only thing that is configured is the Network Level Auth requirement, which I confirmed on the "problem" machine by following steps in my above linked help article.

Best Answer

Since it's a Windows 2012 machine you are trying to remote into using a Windows 7 PC, it might be that you don't have all the necessary Windows Updates for TLS 1.1 & TLS 1.2.

Try installing this Windows Update (KB3080079)

Then restart your PC and attempt to initialize the remote desktop connection.