Update 2:
I started nc locally and pointed the Shelly to my computers ip:port to see if it broadcasts, and I get immediate feedback whenever I toggle the switches:
$ nc -ul 5683
� SHSW-25#C45BBE608884#2�C��
�{"G":[[0,9103,0],[0,1102,"stop"],[0,1103,-1],[0,2101,1],[0,2102,""],[0,2103,0],[0,2201,0],[0,2202,""],[0,2203,0],[0,4102,0.00],[0,4104,0],[0,6103,"normal"],[0,3104,55.00],[0,6101,0],[0,9101,"roller"],[0,4108,227.14]]}P
��cits�
� SHSW-25#C45BBE608884#2�C��
�{"G":[[0,9103,0],[0,1102,"stop"],[0,1103,-1],[0,2101,0],[0,2102,""],[0,2103,0],[0,2201,0],[0,2202,""],[0,2203,0],[0,4102,0.00],[0,4104,0],[0,6103,"normal"],[0,3104,55.00],[0,6101,0],[0,9101,"roller"],[0,4108,227.14]]}P
��cits�
� SHSW-25#C45BBE608884#2�C��
�{"G":[[0,9103,0],[0,1102,"stop"],[0,1103,-1],[0,2101,1],[0,2102,""],[0,2103,0],[0,2201,0],[0,2202,""],[0,2203,0],[0,4102,0.00],[0,4104,0],[0,6103,"normal"],[0,3104,55.00],[0,6101,0],[0,9101,"roller"],[0,4108,227.14]]}P
��cits�
�{"G":[[0,9103,0],[0,1102,"stop"],[0,1103,-1],[0,2101,0],[0,2102,""],[0,2103,0],[0,2201,0],[0,2202,""],[0,2203,0],[0,4102,0.00],[0,4104,0],[0,6103,"normal"],[0,3104,55.00],[0,6101,0],[0,9101,"roller"],[0,4108,227.14]]}
So the Shelly is behaving as expected and broadcasting to the configured target, however my HA instance does not seem to pick up on it.