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5 from 4 votes

Pineapple Upside Down Cake

From scratch vanilla cake with caramelized pineapples and maraschino cherries on top.
Prep Time25 minutes
Cook Time45 minutes
Total Time1 hour 10 minutes
Course: Dessert
Cuisine: American
Servings: 8
Calories: 589kcal
Author: Julie Evink

Ingredients

Topping:

  • c. salted butter (5 ⅓ Tablespoons)
  • c. brown sugar
  • 1 can sliced pineapple rings (20 ounce)
  • 13 Maraschino cherries

Cake:

  • ¾ c. granulated sugar
  • ¼ c. salted butter
  • 1 egg
  • 1 ¼ c. all-purpose flour
  • ½ c. milk
  • 1 Tbsp Greek yogurt plain or vanilla
  • 1 tsp vanilla extract
  • 1 ¼ tsp baking powder
  • ¼ tsp salt
  • ½ c. walnuts chopped or halves

Instructions

  • Preheat the oven to 350 degrees F.
  • Grease and line the bottom of a 9-inch round cake pan (preferably a springform pan) with parchment paper.
  • Melt and stir together the butter and brown sugar and pour into the cake pan. The brown sugar doesn't have to be completely dissolved.
  • Prepare 7 pineapple slices by patting them completely dry with a paper towel.
  • Lay one whole pineapple ring in the center of the brown sugar mixture.
  • Cut 6 pineapple slices in half and around the center pineapple slice on top of the brown sugar mixture.
  • Place a maraschino cherry in the center of each pineapple ring. Set the pan aside.
  • In a large mixing bowl, cream the sugar and butter until light and fluffy.
  • Add 1 egg and mix.
  • Mix in milk, yogurt and vanilla.
  • Stir in flour, baking powder, and salt until just combined.
  • Fold in walnuts
  • Pour the cake mixture evenly over the pineapples in the pan. It’s a thick cake batter, so it helps to dot the batter over the pineapples and carefully spread it to the edges.
  • Put the pan in the oven and bake for 45 or 50 minutes, or until a toothpick inserted in the center of the cake comes out clean.
  • Let sit for about 5 minutes.
  • Loosen the sides with a knife, then turn upside down onto a flat serving dish. (The pan should still be warm when you do this).
  • Serve with vanilla or maple walnut ice cream.

Notes

*I used all but 2 of the sliced pineapple in the 20 ounce can.
How do you store it?
After cooling, store it in the refrigerator in a cake container or covered with plastic wrap. If you don’t have a container, then poke toothpicks in the cake to hold up the plastic wrap to keep it from sticking to the topping.
To freeze, cool the cake and then freeze it for a couple of hours. Wrap it in plastic wrap and aluminum foil. Label it with the date and enjoy it within 2 to 3 months.
What kind of pan is best for this recipe?
I prefer a springform pan because it makes turning the cake out so easy. You can use other kinds so read through these tips:
8-inch round or square pan will make a taller cake and you will need to add baking time. A 9-inch pan will make a flatter one. If you use either of these be sure to line the bottom with parchment paper.
You can also use silicone baking pans. If you do, you don’t need parchment but you should grease them.
You can also use a cast-iron skillet, but I find it’s really hard to get the cake out. If you do use it, be sure to grease it really well and line it with parchment.
Is there a way to make the topping less thick and sweet?
Yes, you can use ¼ cup butter and ½ cup brown sugar for the topping. It will still taste good and work well.
Should I let it cool before turning it out?
It’s better to remove the cake while it’s still warm so the topping doesn’t cool and stick to the bottom.
Also, if something doesn’t come out correctly, you can reattach the topping to the cake and it will congeal together if it’s still warm. So, let it sit for five minutes and then turn it out. Use potholders to protect your hands if the pan is still hot.

Nutrition

Calories: 589kcal | Carbohydrates: 87g | Protein: 8g | Fat: 25g | Saturated Fat: 10g | Cholesterol: 58mg | Sodium: 219mg | Potassium: 312mg | Fiber: 3g | Sugar: 56g | Vitamin A: 525IU | Vitamin C: 7mg | Calcium: 107mg | Iron: 3mg