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Not retransmitting after a TCP retransmission attempt

Please forgive me for asking this question using a translator. I'm a beginner who doesn't know much about networking yet. My app on window operating system is getting connection timeout several times and I captured the packet using wireshark on the server. When I checked it, I realized that the syn segment is not being processed after retransmission attempt at the time of connection timeout. Please help me understand why this is happening.

https://imgur.com/XYz97Eu