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Many times, you’ll find it necessary to have multiple connections to a Remote Desktop server, and by default, Windows Server 2008, Windows Server 2008R2, Windows Vista, Windows 7, etc. limit the number of Remote Desktop Policy Connections to 1 user.

On Windows Server 2008R2, the Restrict Terminal Services users to a single remote session Group Policy setting determines whether you can connect to your existing physical console session. When this option is enabled, when logging on by default, you will be restricted to a single remote session.

In Windows Server 2008R2 Run/Gpedit.msc

Unlike 2008 which refers to the path as Computer Configuration\Administrative Templates\Windows Components\Terminal Services\Terminal Server\Connections node and this is correct for 2008 servers. However the article at MS seems to indicate that the path is the same for 2008R2 however this is not correct. The corrected path is listed below for editing this.

This setting is available in the path Computer Configuration\Administrative Templates\Windows Components\Remote Desktop Services\Remote Desktop Session Host\Connections node of the Local Group Policy Editor. You can also configure this setting in Terminal Services Configuration. The Restrict each user to a single session setting appears in Edit settings in the General section. If you would like to have multiple simultaneous sessions for the same user, please uncheck this setting or set this group policy as Disabled.