Preheat the oven to 350 degrees F (175 degrees C). Grease fluted tube pan (such as Bundt®) with cooking spray with flour.
Pour melted butter into the bottom of the prepared pan. Sprinkle brown sugar evenly on top. Drain pineapple rings over a measuring cup; reserve juice. Cut rings in half. Alternate placing halved pineapple rings and maraschino cherries around the pan. Set aside.
Combine cake mix and pudding mix in a large mixing bowl. Pour enough milk into the reserved pineapple juice to make 1 cup of liquid; add to cake and pudding mixture. Pour in vegetable oil. Mix on low speed, adding 1 egg at a time until blended. Increase speed to medium; mix until thoroughly combined and smooth, about 2 minutes. Pour batter over pineapples and cherries in the pan.
Bake in the preheated oven until a toothpick inserted into the center comes out clean, 33 to 40 minutes. Let cool for 10 minutes before removing from pan.
You can use pineapple cake mix instead of yellow.
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