Unable to access a TS Gateway server – check IIS default web site is running

While carrying  out some hyperV renovations for a client we happened on a problem that I though I would share. The scenario is an internet facing server acting as a Windows 2008 Rs Terminal services gateway to another Windows 2008 R2 server where the application is held. The client has settings on the remote user machines that tell the rdp session to connect to the internet facing server with the details of the backend Terminal server. Prior to our work on the networking and virtual networking aspect of the two physical servers and some hyperV hosted virtual machines on both hosts – all was working.

After we made our changes – dealt with some DNS and DHCP issues – and restructured network card use between virtual machines – we brought both servers back on line only to find we could not access the Terminal Services Gateway server from remote clients and were getting a message to that effect when we tried to connect. We were able to access the Gatway remotely through RDP and the backend server locally through RDP. We checked all the Terminal Server related services were loading and checked the event logs for clues on both machines. Alfter a couple of reboots I wondered what else wasn’t working and rapidly discovered that no IIS related services such as OWA were working remotely or even locally.

This gave us the clues to start checking on IIS and it was here that we found that the default web site on the front end server had not restarted despite several reboots of the physical server. Starting the site manually allowed us to access OWA and also to access the Terminal Server again remotely through the gateway server. So lesson learned – check the logically linked components and find whats not working !!!