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How do I test a port for dropped packets?

Last Modified: 2012-08-13

I have a custom windows service running on a Windows Server 2008 x64. For some reason, 3 out of 10 users are dropping the connection to this server. Before looking into the service, I want to know if the port and connection can handle these amount of users. I want to be able to test the port to see if it can handle connections. How do I go by doing so?
I tried using "Process and Port Analyzer" but it only shows me the traffic and not if a packet has been dropped.

Are therer any tools aout there that will show me this? How many connections can a standard TCP Port (example: 9000) take?

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