So I was called in over the holiday for a Windows Server 2008 update error that a client was receiving when they attempted to update their server. This error is very well documented by Microsoft and there are alot and I do mean alot of things that can cause this error. Well when I started troubleshooting this server it had not been updated since September 2009 which is quite a while to go without any critical updates to a very important server. So this article will talk about trouble shooting this error on a Windows 2008 server incase you ever run into this problem.

The following are the troublshooting steps that I followed according to Microsoft http://support.microsoft.com/kb/836941 but i deviated from some of their instructions based on my own personal experience. After each step you should check your updates.

1. Confirm internet connectivity
   1. You have to be able to access the Internet to download updates.
   2. Goto google.com and microsoft.com to make sure you Internet is working
2. Turn off ALL firewalls including Windows Firewall
   1. To determine whether it is a firewall issue or not you should disable ALL firewals
   2. Microsoft recommends that you disable just third-party firewalls but for testing disable them all
3. Disable anti-virus programs
   1. Anti-virus programs allow will not normally affect updates but new spy-ware and firewall programs that are also anti-virus programs can cause a problem so just disable them for testing.
4. Disable software accelerator programs
   1. Software accelerator programs speed up your internet connection by compressing the information you are downloading.
   2. Sometimes these programs can cause problems with updates where you are downloading programs form Microsoft
5. Add the Windows Update site and Microsoft Update Site to your trusted sites list
   1. So you would think Microsoft wouldn’t block access to their own site but sometimes they do
   2. Add http://update.microsoft.com and http://windowsupdate.microsoft.com to your safe list to allow Windows access to those sites to download updates

Try all those steps listed above and if those still don’t work then try these steps below that I discovered also play a factor in Microsoft Updates.

1. Reboot your server
2. Run Microsoft Updates as an Administrator
   1. Even if you are an administrator this can be a possible problem if you don’t run it as an administrator
3. Check your HOSTS file for bogus entries
   1. %windir%\system32\drivers\etc\HOSTS is a text file of DNS type records
   2. Open this file in notepad and make sure there are no entries for windows updates.
4. Reset your proxy server
   1. type from a command prompt “netsh winhttp reset proxy” (without quotes)
5. Check Group Policy
   1. Group policy has a lot of settings in it that can cause updates to not work properly
   2. Check all settings in group policy that could effect Microsoft updates
   3. You can also check out my article on Group Policy if you are not familiar.

Well there are my steps for trouble shooting this problem and hopefully one of these solutions will fix or at least give you more information on how to fix the problem. If you find that there is another solution please feel free to submit it to me within this post.