Pineapple Upside Down Bundt Cake

Pineapple Upside Down Bundt Cake is a timeless, crowd-pleasing dessert that brings together tender yellow cake, caramelized brown sugar, juicy pineapple, and sweet maraschino cherries in a beautifully dramatic presentation. Baked in a Bundt pan, this version elevates the classic upside-down cake with a stunning ring of fruit and a moist, bakery-style crumb.

The magic happens when the cake is inverted, revealing glossy pineapple slices and cherries nestled in a buttery brown sugar glaze. Thanks to the addition of instant pudding and pineapple juice, the cake stays exceptionally moist and flavorful. Whether served warm or at room temperature, this cake feels nostalgic, festive, and always special.

Ingredients

• ½ cup butter (1 stick), melted
• ½ cup packed brown sugar
• 1 can pineapple rings in 100% juice (juice reserved)
• 1 jar maraschino cherries
• 1 box yellow or pineapple cake mix
• 1 (4-serving) box instant vanilla pudding mix
• 3 eggs
• Vegetable oil (amount called for on cake mix box)
• Milk (to complete liquid measurement)

Best Ever Pan Release (Optional but Highly Recommended)

• Equal parts vegetable shortening
• Equal parts vegetable oil
• Equal parts all-purpose flour

Instructions

1. Preheat the Oven: Preheat your oven to 350°F (175°C). This ensures even baking and proper caramelization of the fruit.
2. Prepare the Bundt Pan: Generously coat a Bundt pan with pan release or non-stick spray, making sure to cover all grooves, edges, and the center tube thoroughly to prevent sticking.
3. Create the Topping: Pour the melted butter evenly into the bottom of the prepared pan. Sprinkle the brown sugar evenly over the butter, creating a rich base for the fruit.
4. Arrange the Fruit: Cut the pineapple rings in half. Arrange them around the bottom of the Bundt pan, alternating with maraschino cherries for a decorative pattern. Set the pan aside once the fruit layer is complete.
5. Prepare the Batter: In a stand mixer or large bowl, combine the cake mix and instant pudding mix. Drain the pineapple juice into a measuring cup and add enough milk to make 1 cup of liquid.
6. Add the liquid mixture, eggs, and the amount of vegetable oil specified on the cake mix box. Mix according to the package instructions until the batter is smooth and well combined.

Baking, Unmolding & Serving