This Pineapple Upside-Down Cake made with a boxed cake mix brings classic retro flavor with very little effort. A buttery brown sugar glaze, perfectly arranged pineapple rings, and bright maraschino cherries bake in a 9×13 pan, then flip out onto a platter for an impressive, crowd-ready dessert.
When warm weather arrives we always turn to pineapple desserts like this and a Pineapple Angel Food Cake. If you want something quick that still tastes homemade, this recipe (like a Lemon Bundt or Orange Juice Cake made from cake mix) is an easy go-to.
It’s ideal for summer cookouts, birthdays, and potlucks when you need a dessert that feeds a dozen with minimal fuss.
Why you’ll love this recipe
- Quick prep: About 10 minutes, since the boxed mix does most of the work.
- Classic flavor: Brown sugar, butter, pineapple, and cherries give that retro taste you remember.
- Crowd-pleaser: Reliable for potlucks, pool parties, and family dinners.
- Serve warm or cold: Enjoy chilled or warm a slice for 15–20 seconds in the microwave.
Ingredients
Notes and substitutions are below. For exact measurements and the printable card, see the recipe card at the end.
- Unsalted butter and light brown sugar: Melt the butter and stir in packed brown sugar to make the caramel topping. Pack the brown sugar firmly when measuring.
- Pineapple slices in juice and maraschino cherries: Use a 20-ounce can of pineapple and a 6-ounce jar of stemless cherries. Drain and pat both dry; reserve the pineapple juice for the batter. Drying the cherries helps prevent color bleed.
- Yellow cake mix, oil, and eggs: One 15.25-ounce box of yellow cake mix prepared according to the package, substituting reserved pineapple juice (topped to 1 cup with water) for the water. Vegetable oil and eggs follow the box directions.
How to Make Pineapple Upside-Down Cake with Cake Mix
Step-by-step instructions below. The printable recipe card contains the full measurements and timings.
Step 1: Preheat the oven to 350°F. Lightly grease a 9×13-inch pan. Stir melted butter and brown sugar until smooth, then spread evenly across the bottom of the pan to form the caramel base.
Step 2: Drain the pineapple, reserving the juice. Pat the slices dry. Arrange pineapple rings over the brown sugar and press a patted cherry into the center of each ring. Tuck extra cherries into gaps as desired.
Step 3: Add water to the reserved pineapple juice to make 1 cup total. Use that liquid to prepare the cake mix along with the oil and eggs called for on the box. Pour the batter evenly over the pineapple and cherries, spreading gently if needed.
Step 4: Bake 35–40 minutes, until a toothpick in the center comes out clean or with a few moist crumbs.
Step 5: Right out of the oven, run a thin knife or offset spatula around the edges to loosen. Place a heatproof platter over the pan and flip it while still warm. Wait five minutes, then lift the pan straight up so the caramel topping releases cleanly. Let the cake cool about 30 minutes before slicing.
Pro Tip:
Flipping while the cake is hot helps the topping release, but letting it sit for 5 minutes after flipping is what prevents drips and ensures a smooth, glossy caramel layer.
Storage
Refrigerator: Cover tightly with plastic wrap or place slices in an airtight container. Keeps up to 3 days.
Freezer: Wrap the whole cake or individual slices tightly in plastic wrap and foil. Freeze up to 3 months; thaw overnight in the refrigerator.
Reheating: Enjoy cold or warm a slice briefly in the microwave for a soft, buttery texture.
Tips for the Best Pineapple Upside-Down Cake
- Pat pineapple slices and cherries dry before arranging to prevent a watery topping and color bleed.
- Spread the brown sugar mixture into an even layer so the topping bakes up glossy and smooth.
- Choose a light-colored metal pan; dark pans can over-brown the bottom.
- Don’t overmix the cake batter—small lumps are fine and keep the cake tender.
- If you don’t have a large platter, a flat baking sheet or sturdy cutting board will work—just be sure it’s heatproof and has a lip to catch syrup.
More Cake Mix Desserts
- Cherry Chip Cake
- Blueberry Cobbler with Cake Mix
- Lemon Bundt Cake with Cake Mix
- Strawberry Jello Poke Cake
- Orange Juice Cake with Cake Mix
Pineapple Upside Down Cake with Cake Mix
Author: Jaclyn
Equipment
-
9 x 13 inch nonstick cake pan
Ingredients
- 6 Tablespoons unsalted butter, melted
- ¾ cup light brown sugar, packed
- 1 can (20 ounces) pineapple slices in juice
- 1 jar (6 ounces) maraschino cherries without stems, drained and patted dry
- 1 box (15.25 ounces) yellow cake mix
- ½ cup vegetable oil
- 3 large eggs
Instructions
- Preheat oven to 350°F. Coat a 9×13 baking pan lightly with non-stick spray and set aside.
- Stir together melted butter and brown sugar until smooth. Pour into the bottom of the cake pan and spread evenly with a spatula.
- Drain pineapple slices, reserving the juice. Pat slices dry with paper towels.
- Arrange pineapple slices and cherries in the pan. Place four rings down the middle and two on either side, with cherries in the centers and tucked in gaps.
- Add water to the reserved pineapple juice until you have 1 cup of liquid.
- Prepare cake mix according to the box, substituting the pineapple juice mixture for the water. Pour batter evenly over the pineapple and cherries.
- Bake 35 to 40 minutes, or until a toothpick inserted in the center comes out clean or with a few moist crumbs.
- Immediately run a thin knife or offset spatula around the edges to loosen. Place a heatproof platter over the pan and flip. Wait 5 minutes before lifting the pan off.
- Allow to cool for 30 minutes before slicing.
Notes
A baking sheet or sturdy cutting board works in place of a platter.
Storage: Cover tightly with plastic wrap or store in an airtight container in the refrigerator for up to 3 days. Serve chilled or microwave briefly to warm.
Nutrition
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