Installing applications remotely on a Windows Server 2008 R2 server

Recently, I needed to set up a 64-bit Windows Server 2008 R2 server from scratch. Installing Windows is nowadays very easy, and doesn't require many steps. Basically, it's just a matter of putting the DVD into the drive, booting, answering a few questions, and then taking a break/nap/C64 emulator session/watercooler chat/cup of coffee for about 20 minutes.

Once the setup is done, the usual next step is to configure few details, enable some roles such as Hyper-V and IIS 7, and then proceed to install applications. If you are like me, you are probably going to use a remote desktop connection to manage your server once you connect it to the network. Since you might not have a suitable file share set up at this point, you might do what I did: enable the remote server session to access local drives from the host computing. This way, you will get access to the installation files from the host PC (the one next to which you are sitting), and then see those files as a network share or drive on the server machine.

All this is very simple to set up (go to the Remote Desktop Connection utility's Local Resources tab, and select Local devices and resources). But, if you try to launch a setup application from the TSCLIENT share, you might get the following Windows Installer message:

[Window Title]
Windows Installer

[Main Instruction]
The Windows Installer does not permit installation from a Remote Desktop Connection.

[OK]

This happens because Windows Installer does not support installing from the "fake" network share created by the remote desktop client (mstsc.exe). A Microsoft Knowledge Base article 927063 talks about this error, but offers in my opinion somewhat complex solutions.

The easy solution: simply copy your installation file (hopefully it isn't overly large!) onto the desktop (using the remote desktop network share; this works well) and then install from the desktop.

Problem solved!