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At times, the CarPlay system in the Chrysler 300 may stop working due to the unpredictable nature of mobile devices and Bluetooth connectivity. In such a situation, the recommended steps would be to detach your mobile device, disable Bluetooth on the Chrysler, restart the car, and then set everything up again. Specifically for iPhones, you can navigate to Settings, General, CarPlay on your mobile device, and choose the option "Forget This Car." Additionally, using the in-dash infotainment unit in the Chrysler 300, you should also forget the connected phone. If re-pairing the devices doesn't resolve the issue, there might be a problem with the head unit itself that would require inspection by a dealership to resolve.
If Apple Carplay isn't functioning properly in your Chrysler 300, attempt resetting the system by toggling the Bluetooth feature on and off, and by disconnecting and then reconnecting your iPhone.