I haven't been able to run Windows Update (now Microsoft Update) on an old Windows 2000 Server box forever, but I rarely turned it on. Now I am finally giving it to my brother and wanted to make sure all the junk was cleared off and the box is updated.

I was getting the error in the title 0x8024402C. A couple years ago I wasn't eager to troubleshoot it as it would involve many hoops in Microsoft's knowledge base, now Google has indexed many forums and the best answer often creeps to the top of their search results.

I found this solution for 0x8024402C: Work around to install MS Updates - Windows Update
You basically just need to go to
HKEY_LOCAL_MACHINE and delete the Connections key from
Software\Microsoft\Windows\CurrentVersion\Internet Settings\

That was it! That's why I could not run Windows Update for years..