Additional info: At Evan's suggestion attempting to hit https://184.108.40.206 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://220.127.116.11 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 18.104.22.168:443 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?