Windows – WSUS synchronization to Microsoft

windowswsus

Additional info: At Evan's suggestion attempting to hit https://65.55.185.26 through IE fails on this server. However, using standard HTTP instead (without SSL) brings up the Windows Update page. Other servers behind the same firewall can hit https://65.55.185.26 no problem, so it's not a gateway issue.

Windows Firewall is on, but there don't seem to be any outbound rules blocking https connections. I will try other https sites, and disable Windows Firewall as a next step.

Original Question
I have a problem with Windows Server Update Services SP2, where the synchronizations to Microsoft are
failing. Only those synchronizations are failing; all client computers are able to receive updates that have already been approved.

The synchronization error is as follows: 

WebException: Unable to connect to the remote server ---> 
System.Net.Sockets.SocketException: A connection attempt failed because the 
connected party did not properly respond after a period of time, or 
established connection failed because connected host has failed to respond 
65.55.185.26:443

at System.Net.HttpWebRequest.GetRequestStream() 
at System.Web.Services.Protocols.SoapHttpClientProtocol.Invoke(String 
methodName, Object[] parameters) 
at 
Microsoft.UpdateServices.ServerSyncWebServices.ServerSync.ServerSyncProxy.GetAuthConfig() 
at 
Microsoft.UpdateServices.ServerSync.ServerSyncLib.InternetGetServerAuthConfig(ServerSyncProxy proxy, WebServiceCommunicationHelper webServiceHelper) 
at 
Microsoft.UpdateServices.ServerSync.ServerSyncLib.Authenticate(AuthorizationManager 
authorizationManager, Boolean checkExpiration, ServerSyncProxy proxy, Cookie 
cookie, WebServiceCommunicationHelper webServiceHelper) 
at 
Microsoft.UpdateServices.ServerSync.CatalogSyncAgentCore.SyncConfigUpdatesFromUSS() 
at 
Microsoft.UpdateServices.ServerSync.CatalogSyncAgentCore.ExecuteSyncProtocol(Boolean allowRedirect)

I have traced the day this started happening as the day we installed
Terminal Services Gateway on this server. I now know that TS is incompatible
with WSUS, so I have removed TS Gateway and the included options, however I
am still receiving the error.

I attempted to re-install WSUS (using the existing updates and database) and there is no change.

Running Network Monitor on the server, it appears that WSUS sends traffic to the Microsoft server, however it receives nothing in return. I have confirmed we have no outgoing firewall rules blocking the traffic, and to my understanding, since WSUS is initiating the connection, there should be nothing else required to allow the connection to proceed.

Has anyone come across this, or know of a solution?

Best Answer

Opening https://65.55.185.26 on the server computer ought to give you a Windows Update page. If it doesn't, you've got communication issues.

I'm happy to see you're using Network Monitor to see what's on the wire. When you say "it receives nothing in return", are you saying that you're seeing TCP SYN requests going to 65.55.185.26, port 443, and not seeing anything coming back at all?

If you're seeing nothing coming back from 65.55.185.26 then you should start sniffing at the border of the network to see if the server's requests are making out to the Internet or not (and, if they are, seeing if response are coming back). This has the feel that something is firewalling either your requests outbound or the responses coming back.

Related Topic