Windows Server 2008 is stuck at "configuring updates - stage 3 of 3 - 0% complete"

Question

This has happened the last two times I've done updates to this system, and I really have no idea what is going on. It is installing a only a month's worth of updates. It only responds to ping and no services are up, so I can't view the system remotely (I have to hook up a monitor to see this message). In the past I've just restarted the system at this point and it eventually finishes updating. I want to know what I can do to avoid this situation, how to diagnose what is going on, and how to get any kind of remote access during the updates.

Edit: I can start the machine in safe mode (where I did nothing but backup some files). I restarted and it no longer tries to do a windows update, just goes to the desktop where everything seems extremely broken. I can click on some things, but not launch most programs. I guess all I can do at this point is do a system restore or something.

Edit: Re-installed windows on this system yesterday. That's my usual solution to issues I don't feel like diagnosing, like this one.

Solution

Are you running IIS with SSL certs (or anything that requires the certificate store) on the server? I've seen this cause this sort of problem before. I blogged about this on my blog. Scroll past me ranting about Dell's support to the actual information about the problem and the solution.

Comments

[jornane]

How long did you wait? I have experienced Windows servers needing multiple hours to update.

[Algorys]

So networking issues may be affecting the ability to install updates that have already been fully downloaded? Great.