If you have a need to hear sounds coming from your Windows Server 2008, you'll need a sound card or motherboard with sound support, then simply follow steps 1 and 2 below, and you're all set.
A far more likely scenario would be for you to want sound support for your RDP connection (aka, Remote Desktop Connection, aka Terminal Services). This can be useful, say for hearing your largely "head-less" server console, should software be beeping to get your attention. I found bits and pieces of the steps required to get server variants to do the basic level of multimedia. I've now pulled it all together for you here, 10 simple steps, screenshots not really required, but video below if anything trips you up.
How to enable remote sounds in all Windows Server 2008 versions, including all Home Server 2011 variants:
- Go to your Windows Server 2008 desktop, click Start, type services.msc, and hit Enter
- Scroll down to "Windows Audio" service, change Startup type from Manual (the default) to Automatic, then click Start, then OK
- Go to your Windows Server 2008 desktop, click Start, type tsconfig.msc, and hit Enter
- Right-click on the Connection Name "RDP-Tcp" entry, choose Properties, Client Settings tab
- Under Redirection, Disable the following, turn off the checkbox on "Audio and video playback" and hit OK
- Go to your own local system that has sound, and click Start, type mstsc.exe, which launches Remote Desktop Connection
- Click Options, Local Resources, Remote audio, Configure remote audio settings, Settings button
- Choose Remote audio playback, turn on "Play on this computer" radio box and click OK
- Click Connect
- Now on your Windows Server 2008 remote desktop, click Start, type mmsys.cpl and hit Enter, right-click on the "Remote Audio" device and choose Test, and you'll hear sound, that's it!
You are now all set, even after rebooting, you'll now have sound. You may also notice that when you use RDP to login after a fresh reboot, you may notice the subtle Windows Startup sounds.