Just to be clear, GlassWire doesn’t make you repeatedly allow the same program over and over. It makes you allow only new applications. When a program/application changes it is no longer the same thing. For example malware could do something to your allowed application and change it.
Currently GlassWire detects when an application has changed, then you should once again allow the application. Most firewalls work this way.
Unfortunately allowing any application with the same name to access the network isn’t a serious solution because someone could put malware on your PC and call it the name of a popular program and it could do whatever it wants.
For example I could call malware chrome.exe, then it would just bypass our “Ask to connect” mode.
There are some solutions posted above, for example our default “Click to block” mode. Meanwhile we’ll consider making signed certificates an option.
But even if we do use signed certificates if you choose to use “Ask to connect” mode and if you choose to install a lot of different applications all the time you will continue to get “Ask to connect” prompts. So if this is the type of thing you do then we’d recommend our “Click to block” mode that we originally made as a solution to the problem for people who don’t want a lot of prompts, but who still want to see what’s going on with their PC in real-time.