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We have a .NET 3.5 web service that runs just fine when it calls an external web service as long as our web service is installed on Windows Server 2003. When our web service is installed on Windows Server 2008 our outbound web service call is never made. We've replicated this behavior on about 5 different 2008 servers with the exact same issue. We are wondering if it is because the URL address of the service we are calling doesn't end with a file name, it looks like this: https://......./ws/SomeService?applicationName=123

We know this line of code is being executed: Dim result As IAsyncResult = CType(request.BeginGetRequestStream(AddressOf sendCallback, request), IAsyncResult)

However Fiddler shows that NO request is ever being made to https://......./ws/SomeService?applicationName=123

If we move our application to a Windows 2003 server it works perfectly.

If anyone has any suggestions I would greatly appreciate your help.

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It turns out the error we experienced was due to a change on our 3rd party web service's end whereby they had changed something with their authentication mechanism that caused the authentication to fail and somehow that stopped the request from ever appearing in Fiddler due to the failed authentication. Their service is written in Java and I don't know much about their servers. I hope that helps someone.

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