Combine the milk, yeast, and 1 tsp of sugar. Let sit for five minutes, or until foamy.
In a large bowl, combine ¼ cup white sugar and flour. Add the milk/ yeast mixture, egg, melted butter, and vanilla and stir until well combined.
Dump your dough onto a floured surface and knead for 5 minutes, or until the dough is no longer sticky.
Cover your dough with plastic wrap or a dish towel and allow your dough to rise for 20 minutes.
Roll out the dough into a ½ inch thick sheet and cut out 4-inch circles.
Allow your cut donuts to rise for another 20 minutes. While they rise, preheat the air fryer for 4 minutes at 350°F.
Cook 3 donuts at a time for 3-5 minutes at 350°F.
While the donuts are cooking, prepare the filling by smashing it with a fork. The goal here is to break up any large chunks of cherry.
Once donuts are fully cooked, immediately use a piping bag to fill each donut with the pie filling.
Allow to cool slightly.