Wi-Fi Network Authentication Required dialog pops up every so often for no reason

Hello, I am running a Rasp Pi 5 with it's default OS and it's fully updated. I've been having an issue where, despite the WiFi being rock solid, this dialog pops up every few days on top of the POS (Point of sale) script I am running. See screenshot.

1. Why is the dialog opening up to begin with? The device has the SSID+Password already, it's saved, so even if it were to disconnect for a short period of time, it should auto-reconnect silently in the background like all of my other non-Pi Linux devices. (which never get this dialog ever)
2. Can I run my PyGame/SDL2 Window in some sort of Always-On-Top way in Linux? I want nothing to ever render over top of my POS process.

Any help would be greatly appreciated.