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Microsoft Update scanning loop

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I have a machine that runs Microsoft Server 2003. I need to get it fully updated. When I click on Microsoft Update and have it look for updates, the screen stays at Checking for the latest updates for your computer... it seems to get stuck in a scanning loop. I messed with the Automatic Updates settings but they never registers any new updates either. I know there are new updates available, it hasn't been updated in a while.

Does anyone have any idea how I can get this machine updated?
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