I have noticed when Glasswire is set to Ask to Connect the popup shows asking for permission for the software to connect to the internet. However when it does this, it drops the initial connection by the time it takes you give it permission. Then the next time it tries to connect, it is allowed.
The default for this shouldn’t be to immediately drop the connection, there should be a time limit “keep alive” until the user gives it the proper permission. Probably unlimited until the user either allows or blocks the connection and creating the new rule. I have used other firewalls which handle this in the fashion described.
This would also fix this problem.