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    <p>You said that you are doing 5 outgoing request for each incoming request to the ASP page. Is that 5 different servers, or the same server? </p> <p>DO you wait for the previous request to complete, before issuing the next one? Is the timeout happening while it is waiting for a connection, or during the request/response? </p> <p>If the timeout is happening during the request/response then it means that the target server is under stress. The only way to find out if this is the case, is to run wireshark/netmon on one of the machines, and look at the network trace to see if the request from the app is even making it through to the server, and if it is, whether the target server is responding within the given timeout.</p> <p>If this is a thread starvation issue, then one of the ways to diagnose it is to attach windbg.exe debugger to w3wp.exe process, when you start getting timeout. Then load the sos.dll debugging extension. And run the !threads command, followed by !threadpool command. It will show you how many Worker threads and completion port threads are utilized/remaining. If the #completionport threads or worker threads are low, then that will contribute to the timeout.</p> <p>Alternatively, you can monitor ASP.NET and System.net perf counters. See if the ASP.NET request queue is increasing monotonically - this might indicate that your outgoing requests are not completing fast enough.</p> <p>Sorry, there are no easy answers here. THere is a lot of avenues you will need to explore. If I were you, I would start off by attaching windbg.exe to w3wp when you start getting timeouts and do what I described earlier.</p>
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    1. POHow to diagnose "the operation has timed out" HttpException
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    1. COThe outgoing requests (and incoming for that matter) are all on one server with one IP address (Ethernet 10meg). Attempts are now made synchronously only because I wanted to ensure the code was working before converting to asynchronous. The asp.net -> requests queued counter is rarely non-zero so that does not lead anywhere. The volume of requests really limits the use of a debugger or wireshark tool. Finding one of 100 daily timeouts in an average day of over 1M requests, is tough. Many thanks for your comments.
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    2. COIt's not that difficult - just attach windbg.exe to the W3WP process when you start getting timeout exceptions, dump the process (.dump /ma <filename) and detach debugger. Then you can restart debugger, load the previously created dump, and debug away...
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