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TCP ACK question

Dear Community,

 

Dear Community,

 

I am facing an issue where we are seeing intermittent application connection failures between an internal server and a cloud based DB. When I did a packet capture I found that the failures coincide with the Cloud DB sending TCP Resets. I attached the pcap output. My theory is that when the internal server sent the ACK on packet 3929, it immediately tried to start the TDS data stream on packet 3930 thinking that the TCP connection had been established. But, what if the cloud DB never received the ACK packet sent on packet 3929? Would that cause the "The acknowledgment number field is nonzero while the ACK flag is not set"? Ive never really considered what would happen if the remote end never actually received the ACK packet during the TCP 3 way handshake. I am suspecting some kind if possible congestion or packet loss during the TCP 3 way handshake as well because the initial SYN packet 3926 had to be Retransmitted because it never received a SYN/ACK. 

 

Any insights you can lend would be very helpful. Thanks!

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