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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.

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How long did you wait? I have experienced Windows servers needing multiple hours to update. –  yorn Jul 1 at 5:22

4 Answers 4

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.

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There is a KB article: http://support.microsoft.com/kb/949358/en-us from Microsoft to address this. The KB is for Windows Vista/7 but since the codebase is shared, a call to MS can verify whether there is a Win2k8 patch as well.

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I had this issue recently with SBS 2011, it was a real pain in the neck. It turned out it was to do with the Software Protection service not starting, which in turn wasn't working because ipv6 wasn't enabled. If you've disabled ipv6 on your network interface this might be worth looking in to. I just left it overnight and it eventually logged in with tonnes of service failures, I then enabled ipv6 and restarted the updates and away it went. I've been trying to find a way to remotely enable ipv6 on an interface, either connecting via regedit and remote registry and psexec with netsh, but I can't seem to find a way.

If you have any secondary NICs that are unconfigured and are still enabled you might try to plug the network cable in to this on a subnet with a DHCP server, this will give it an auto-configured IPv6 address, then connect to it's temporary address with the services MMC and start software protection, this might get the update going again.

<-- edit -->

I hadn't seen your edit seeing it was broken, the only thing I can suggest would be to try a rollback or uninstall the updates and then maybe try the above if you still trust/need the update.

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So networking issues may be affecting the ability to install updates that have already been fully downloaded? Great. –  Chris Jun 23 '11 at 16:55

Microsoft released a hotfix for this issue.
KB2379016: A computer that is running Windows Vista or Windows Server 2008 stops responding and hangs at the "Applying User Settings" stage of the logon process

To work around the issue without installing the hotfix, create a DependOnService registry key to modify the behavior of HTTP.sys. This makes HTTP.sys depend on crytosvc service to be started first. To do this, follow these steps:
1. Click Start, type regedit in the Start Search box, and then press ENTER.
2. Locate and then click the following registry subkey:
HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\HTTP
3. On the Edit menu, point to New, and then click Multi-string Value.
4. Type DependOnService, and then press ENTER.
5. Right-click DependOnService, and then click Modify.
6. In the Value data box, type CRYPTSVC, and then click OK.
7. Exit Registry Editor.
8. Restart the computer.

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