"If → the wireless network → is connected ..." not triggering on personal wifi

[Airy]

I see two possible causes. One is the version of macOS you are using. Explanation here:

Sonoma Wireless Compatibility

Unfortunately, macOS Sonoma restricts access to the wifi information without Location Permissions, but does not prompt users for such permission when the wifi information is requested. Further, there is no way to manually add Location Permission. So currently, the wifi facilities (including the Wireless Network trigger, Wireless Network condition and WirelessNetwork token) will not work with any version of Keyboard Maestro in Sonoma. To resolve this, Apple will need to either provide a way to m…

Another is that you don't have your permissions set up to allow KM to access location. Instructions here:

https://wiki.keyboardmaestro.com/token/WirelessNetwork

But the first thing I would do to troubleshoot this is open the KM Debugger, check "Pause New Macros" then see if the macro actually runs, and if so execute step by step through the macro. The debugger is really your best friend when it comes to troubleshooting. I find this method easier and more powerful than checking the log.