Pineapple Upside Down Cake

This old-fashioned Pineapple Upside Down Cake recipe comes straight from my grandma’s kitchen and has been a family favorite for generations. With a few special touches that set it apart from the classic version, it’s a homemade dessert that’s just as perfect for holidays as it is for Sunday dinner.

Growing up, this Pineapple Upside Down Cake made an appearance at just about every family gathering. It was one of those desserts everyone looked forward to, right alongside favorites like my Lazy Day Cake. Between the buttery brown sugar topping, juicy pineapple, sweet maraschino cherries, and the unexpected crunch from the walnuts, it was always one of the first desserts to disappear. Now I get to make it for my own family and friends, and it never fails to end with someone asking for the recipe.

What Makes This Recipe Special

This old-fashioned Pineapple Upside Down Cake recipe is a true scratch cake that’s been passed down through my family for generations and includes a few special touches that set it apart from the classic version.

• Cake Flour: Creates a soft, tender crumb with a light texture that’s hard to beat.
• Reserved Pineapple Juice: Instead of letting it go to waste, a little pineapple juice is added to the cake batter for extra flavor and moisture.
• Walnuts: Tucked beneath the pineapple, walnut halves add a subtle crunch that balances the sweetness.
• Pineapple Tidbits or Crushed Pineapple: Instead of traditional pineapple rings, every bite is packed with sweet pineapple flavor.

Looking for another easy homemade cake recipe? My Lemon Poke Cake is another family favorite that’s perfect for any occasion.

Ingredient Notes

See the printable recipe card below for the full list of ingredients and amounts.

• Pineapple: Use canned pineapple tidbits or crushed pineapple, then reserve ½ cup of the juice for the cake batter. This gives every bite sweet pineapple flavor.
• Walnuts: My grandma always used walnut halves beneath the pineapple for a subtle crunch. If you’re not a fan of nuts, you can simply leave them out.
• Cake Flour: Cake flour gives this cake its soft, tender texture and helps create a lighter crumb than all-purpose flour.

How to Make Pineapple Upside Down Cake

Step 1. Preheat the oven to 350°F. Melt the butter in a 9-inch round cake pan. Drain the pineapple, reserving ½ cup of the juice for the cake batter. Arrange the maraschino cherries and walnut halves in the bottom of the pan.

Step 2. Sprinkle the brown sugar evenly over the walnuts and cherries.

Step 3. Top evenly with the pineapple. Set aside.

Step 4. In a large mixing bowl, cream together the shortening and granulated sugar until light and fluffy.

Step 5. Beat in the egg and vanilla extract until fully combined.

Step 6. In a separate bowl, whisk together the cake flour, baking powder, and salt.

Step 7. Gradually add the dry ingredients to the shortening mixture, alternating with the reserved pineapple juice. Mix just until combined, being careful not to overmix.

Step 8. Spread the cake batter evenly over the pineapple layer.

Step 9. Bake for 45-50 minutes, or until a toothpick inserted into the center comes out clean or with a few moist crumbs.

Step 10. Let the cake rest for 5 minutes, then carefully run a knife around the edges. Place a serving plate over the pan and carefully invert the cake. Allow the pan to sit for about 30 seconds before lifting it away. Serve warm or at room temperature.

Baking Tips

• Drain the pineapple well: Too much excess liquid can make the topping soggy.
• Use a metal or nonstick cake pan: Both work well, but avoid glass pans, which can bake differently.
• Don’t overbake: Check for doneness by inserting a toothpick into the center of the cake. It should come out with just a few moist crumbs.
• Wait 5 minutes before you flip: Let the cake rest briefly after removing it from the oven, then carefully invert it onto a serving plate.
• Run a knife around the edges: This helps loosen the cake so it releases cleanly from the pan.

Storage

• Room Temperature: Cover the cake tightly and store on the counter for up to 2 days.
• Refrigerator: For longer storage, keep the cake covered in the refrigerator for up to 5 days. Let it come to room temperature or warm individual slices before serving. If you love fruity desserts, my Hawaiian Dream Cake is another family favorite that’s perfect for holidays, potlucks, and special occasions.
• Freezer: Wrap the whole cake or individual slices tightly in plastic wrap and aluminum foil, then freeze for up to 3 months. Thaw overnight in the refrigerator before serving.
• Reheating: Warm individual slices in the microwave for 15-20 seconds to soften the brown sugar topping and bring back that fresh-from-the-oven flavor.

Pineapple Upside Down Cake Recipe FAQs

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