TechTips - Remote Desktop Repeatedly Prompts for Username and Password Using Windows Server 2008 R2

I found yet another weird issue with one of my newly built Windows 2008 Servers, when I was trying to let someone remote into the machine they were getting a prompt over and over for their username and password. I found that I not only had to give them permissions but I also had to make a slight change to the default settings of the remote desktop tools. It's a simple fix that might not even affect you.

So first off what is going on with my machine? Why didn't it allow me to connect to the server?

This prompt is caused by a setting in the configuration of the Windows Server 2008 R2 remote desktop that makes a request for the connecting PC to send a statement of health before the connection will be allowed. When this option is enabled it causes all sorts of connection issues if you don't have additional connection properties allowed for network access. Your PC won't be able to connect to the server until you turn off this "Statement of health" option, until you turn it off you will be prompted over and over for your login information.

So how do you turn this option off?

You will need to perform the following steps to turn off the "Statement of Health" request:

Login to your remote server that is giving you the issue (probably at the machine since you can't remote in)

Click Start

Click Administrative Tools

Click Desktop Services

Click Remote Desktop Gateway Manager

Right Click Remote Desktop Gateway Services

Choose Properties

Click RD CAP Store Tab

Uncheck box next to "Request Clients to send a statement of health"

Click OK

After you have changed the setting then you can reboot your machine and the setting should start working. You should be able to remote into the machine without any more repeated prompts for user name and password. This issue doesn't usually affect Vista or Windows 7 users, both have the ability to send the "Statement of health" and probably won't have this issue. Windows XP doesn't have a way to send this "Statement of health" and is the primary target for this fix.