Gather all ingredients. Preheat the oven to 350 degrees F (175 degrees C). Grease an 8-inch pan with cooking spray.

Drain pineapple slices; set aside.

Stir brown sugar and melted butter together in the prepared pan; spread evenly over the bottom of the pan. Place pineapple slices in a single layer on brown sugar mixture. Place a cherry into the center of each pineapple slice and the center of the pan.

Beat cake mix, cold water, and egg together in a large bowl with an electric mixer on low speed for 30 seconds. Beat on medium speed for 3 to 4 more minutes.

Pour batter evenly over pineapple and cherries in the pan.

Bake in the preheated oven until a toothpick inserted into the center comes out clean, 25 to 30 minutes. Cool in the pan for 5 minutes.

Loosen edges and turn out onto a serving platter.