There might be some information in the “dmesg” or the “/var/log/syslog” about why the wifi connection is failing. But this looks more like a wifi hardware problem in the RPi Zero.
There is one fairly easy way to rule out or confirm the hardware problem by using an external USB wifi adapter.
Since you are using a RPi zero you would need to use a USB hub with an external USB wifi adapter OR disconnect the prostick for the external USB wifi adapter during the test.
You can disable the internal Raspberry Pi Zero wifi adapter by setting rfkill to yes.
piaware-config rfkill yes
With rfkill on, piaware’s boot system will look for any connected wifi USB adapters and setup with the same ssid and password you have in your piaware configuration on the wifi adapter.
You can go back to the internal wifi connection by turning rfkill back to no.