Windows Updates Failing on Server 2008 R2

I’ve seen a really strange error with Windows updates on some 2008 R2 servers where they fail to start downloading and installing updates. They can connect to Windows Update and find available updates, but once you select them and start the process off they fail after a few minutes. I’d tried all sorts, including rebooting and all the usual stuff.

The solution I found was probably the most unlikely thing I’ve ever seen, but here it is. On the notification tray, click the double up arrows and click customize;

Then tick the “Always show all icons and notifications on the taskbar” checkbox and ok out of the dialogue;

This then allowed me to start the updates downloading and installing. I think it’s something to do with Windows update not being able to create the taskbar icon in the notification area and the subsequent balloon notification that says updates are downloading, but that’s just a wild theory of mine, I have no proof that’s what it is.

I know the whole solution sounds a bit mental, but I’ve done this on a fair number of servers that were playing up with regards to downloading updates now and it’s always worked.