Why does my request end in timeout?

edit

Client at 192.168.1.100, server at 192.168.1.5.

At 23:34:43 the client logged a timeout (System.Net.WebException: timeout during a web request).

Communication is encrypted via TLSv1.2.

Packets around this time:

This happens randomly. Is the client doing anything wrong? It looks the client is deciding to close the connection and open a new one, but I'm not sure if there's anything weird with the packet sequence.