Preheat oven to 350F. Spray jumbo muffin tin with cooking spray. I only have one 6 count Jumbo pan, so if you have more than one — you’ll need up to 18 cups. If you only have one like me, you can also use a 9×9 pan for the extra batter.
Mix melted butter and brown sugar and spoon a bit into the bottom of each muffin cup (and smatter around the 9×9 if you are using one).
Picking up one pineapple slice at a time, place the pineapple into the muffin cup on the brown sugar/butter mixture (reserve the pineapple juice in the cans for the next step!). Then place a cherry right in the middle of the pineapple circle hole (isn’t this cute?!?)
Prepare the cake mix according to the back of the box — but instead of water use the pineapple juice from the slices cans. Use a 1/3 cup measuring cup or cookie scoop to put batter into the cups on top of the pineapple and cherry.
Bake in the oven for 20 – 25 minutes or until a knife comes out clean. Let them sit in the pan for a few minutes before attempting to remove. Use a knife to loosen the sides of the cakes and place a clean cookie sheet on the bottom of the cakes and flip over, tipping the cakes out onto the cookie sheet.