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On my Win7 laptop, I add the media to Windows Media Player and allow my library to be shared, but in the outdated Windows Server 2003, I can't figure out how to stream anything. Windows Media Player 10 (the latest version I can get on this server) doesn't seem to have a streaming option. I've tried the streaming role for the server, but that seems to be completely different than what I'm trying to do.

To be clear, it's not a networking issue. They're both wired on the same network and can see each other easily. It's a feature issue where the server has no software that'll stream to the xbox.

Aside from replacing or updating the old OS, what I can do to stream from it to my 360?

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I ran into issues trying to stream from windows XP to my Xbox360. The Xbox would randomly drop out when it actually appeared at all. I believe the issue is that WMP10 support for the 360 is not as good/friendly as WMP11. I wrestled with it for a month or two and finally switched to windows 7. –  Lee Harrison Sep 10 '12 at 18:34
    
This server is running other things that Win7 can't, like Team Foundation Server. Not to mention it's pretty old hardware. If I had to choose between TFS and streaming to my Xbox, TFS wins for me anyway. –  Corey Ogburn Sep 10 '12 at 18:37
    
Completely understandable. And TBH the streaming features aren't that great, and I experience severe input lag on the 360 when navigating through my media located on my desktop. DNLA may be another option if you setup your machine as a DNLA server. Then you may be able to use it from your 360, though I have never experimented with this. –  Lee Harrison Sep 10 '12 at 20:57
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