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I have a problem seen on Windows Server 2008 running IIS 7. I have seen a packet trace where the server stops responding to SYN from clients. However, it will respond to intermediate SYNs i.e

Say Client A sends SYN 1 at time t1.
Server will not respond
Client A now sends SYN 2 for a *different* connection at time t2 (t2 > t1)
Server responds.
Client A retransmits SYN 1 . 
Server fails to respond

Ultimately client A times out. How do I find the reason why server is not responding to one particular connection.

Are there TCP stats that one can see on the Windows Server?

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up vote 1 down vote accepted

Make sure to packet sniff on both sides of the connection. You may see the SYN being sent, but maybe it never actually reaches its destination. Something filtering?

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