Heat up a large non-stick pan over medium heat and sauté the pineapple with the vanilla and cinnamon. Once they begin to break down and the juices begin to release its natural sugars, remove from heat.
Assemble:
On a flat surface, place 4 bowls or lidded glass jars. Fill each with ½ cup oats, ¾ cup milk, and stir.
Divide pineapple mixture into each of the four jars.
Chop the cherries and add them to the oat mixture, stir to combine.
Refrigerate:
Refrigerate for 4-6 hours or overnight. Eat cold or warm up for 30 seconds in the microwave.