Using the Alexa app and the Alexa location based reminder feature it would be possible to have Alexa remind you, either when arriving at a specific location or when leaving a specific location to "Don't forget your mask." You can add multiple locations in addition to the Work and Home locations so if you only go to a few locations you can set up a separate reminder for when you arrive at one of the saved locations. Alternately, when leaving your Home location, Alexa could remind you to "Be sure to wear your mask." each time you leave your home location. Alexa is not aware of the vehicle settings, only day/time and the phone's location via GPS. I have set a reminder for each Thursday at 5PM to put out the recycling bins. I have another reminder set to remind me to pay a specific bill on the 1st of each month.