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John, I cannot believe I overlooked the obvious. I have a GPO for enabling RDP services and the scope covers the different subnet but did not include the VPN subnet. I am not sure why previous versions of Windows did not accept the GPO literally and allowed sessions over the VPN. I have modified the GPO to include the VPN subnet and all is working now.
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John, I cannot believe I overlooked the obvious. I have a GPO for enabling RDP services and the scope covers the different subnet but did not include the VPN subnet. I am not sure why previous versions of Windows did not accept the GPO literally and allowed sessions over the VPN. I have modified the GPO to include the VPN subnet and all is working now.

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Thanks for the update and I am glad you got it working.
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Thanks for the update and I am glad you got it working.

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I have an ASA5510 and am using the Cisco AnyConnect Secure Mobility Client v.3.1.09013. The VPN connection works fine, I can browse network shares, access network resources and RDP or SSH into any server on the corporate LAN except for Windows 2012 R2 servers. The server do respond to a ping over the VPN. When I am in the office on the corporate LAN I can RDP into the Windows 2012 R2 servers without issue. We have a mix of Windows 2003 and Windows 2008 R2 servers along with some Linux machines and they all connect without fail. The behavior is consistent on OS X, Windows 7 and Windows 10. Has anyone else experienced this issue?
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I have an ASA5510 and am using the Cisco AnyConnect Secure Mobility Client v.3.1.09013. The VPN connection works fine, I can browse network shares, access network resources and RDP or SSH into any server on the corporate LAN except for Windows 2012 R2 servers. The server do respond to a ping over the VPN. When I am in the office on the corporate LAN I can RDP into the Windows 2012 R2 servers without issue. We have a mix of Windows 2003 and Windows 2008 R2 servers along with some Linux machines and they all connect without fail. The behavior is consistent on OS X, Windows 7 and Windows 10. Has anyone else experienced this issue?

Can't RDP into 2012 R2 across VPN

A virtual private network (VPN) is a network that uses a public telecommunication infrastructure, such as the Internet, to provide remote offices or travelling users access to a central organizational network securely. VPNs encapsulate data transfers using secure cryptographic methods and other security mechanisms to ensure that only authorized users can access the network and that the data cannot be intercepted.

Windows Server 2012 is the server version of Windows 8 and the successor to Windows Server 2008 R2. Windows Server 2012 is the first version of Windows Server to have no support for Itanium-based computers since Windows NT 4.0. Windows Server 2012, now in its second release (Windows Server 2012 Release 2) includes Foundation, Essentials, Standard and Datacenter, and does not support IA-32 or IA-64 processors.

Windows Server 2012

Cisco PIX is a dedicated hardware firewall appliance; the Cisco Adaptive Security Appliance (ASA) is a firewall and anti-malware security appliance that provides unified threat management and protection the PIX does not. Other Cisco devices and systems include routers, switches, storage networking, wireless and the software and hardware for PIX Firewall Manager (PFM), PIX Device Manager (PDM) and Adaptive Security Device Manager (ASDM).