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We have a server where multiple web application are hosted. Users will upload files to the website that will get saved to server HD. Now and then, C: is running out of space because of the uploaded files and all the websites are in trouble and they go down.

Is there any option in Windows 2003 server to alert / send email to the administrator when C: exceeds a certain memory space?

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Yes - you can use the EventTriggers command to "attach a task to an event."

Check out these guys:

and here is someone doing what you're looking for:

Good luck! It gets easier in Server 2008.

Edit: look for this event -

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You really need a third-party monitoring solution for something like that. You could write something custom to do it, but a third-party monitor will serve you better because it will not be caught in any space issues. You should also look at moving the websites to a non-system volume if possible to prevent OS crashes.

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