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Web Forwarders frequently failing for some clients and not others

When the problem exhibits itself, the client gets the common connection timed out from the web browser. I ran a capture focusing on the ip address that the forwarder resolves to and get a tcp handshake with a lot of retransmissions but I'm not seeing anything really jumping out at me to further troubleshoot. Other systems on the network can access the site without problems. I'm suspecting our firewall is monkeying with the packets but the problem seems to come and go and switch which systems are impacted.