Forefront TMG on Windows Server 2008 Core R2

To continue the unsupported series I decided to try to install Forefront TMG on Windows Server 2008 R2 over the holidays after a discussion with Kent Nordström from XP Services and Martin Lidholm from Lidholm&Co. This proved to be an impossible mission though since prerequisites are impossible to install on a Core-installation.

Failures

First failure: Installing SQL Server 2008 Express Edition.
Did this manually, came a little further.

Second failure: Prerequisite check doesn’t work due to usage of legacy technology on the TMG part.
Error message:
15:36:57 ISA setup CA INFO : Running command line: C:\Windows\system32\servermanagercmd.exe -inputpath “D:\FPC\\PreRequisiteInstallerFiles\WinRolesInstallSA_Win7.xml”…

Well, servermanagercmd isn’t around anymore and is replaced with PowerShell. So even if all the roles were to be installed, it’d still fail. Probably possible to copy servermanagercmd.exe from a 2008 Core just to fool the installer.

Prerequisites

The prerequisites for TMG states that the following roles/features need to be installed:

Network Policy Server (not possible on Core)
Routing and Remote Access Services (not possible on Core)
Active Directory Lightweight Directory Services Tools
Network Load Balancing Tools
Windows PowerShell
Microsoft .NET 3.5 Framework SP1
Microsoft Windows Installer 4.5
Windows Update
Windows Web Services API

Conclusion:

Server Core would be a perfect platform for TMG considering the attack surface, less services, less patching and so on. The management of TMG / Server Core is done remotely anyway so the lack of a GUI wouldn’t be negative either. I’d like to see a special build from Microsoft where the prereqs are installed (like the Hyper-V SKU where clustering is included).