Loads of sweet, caramelized pineapple and the softest, buttery rich yellow cake combine to create one of the most gorgeous, delicious Homemade Pineapple Upside Down Cakes around!
4tablespoonsbutterroom temperature, divided into 2 tablespoon & 2Tbsp
1cuppacked brown sugar
20 ounces canned pineapple ringsdrained and patted dry
Cake Batter
1stickbutterroom temperature
¾cupwhite granulated sugar
2largeeggsroom temperature
1teaspoonpure vanilla extract
2cups all purpose flour
1teaspoonbaking powder
½teaspoonbaking soda
½teaspoonsalt
⅓cupwhole milkroom temperature
8ouncescrushed pineapple (in pineapple juice, not syrup) NOT drained
¼cupsour creamroom temperature
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Instructions
Preheat oven to 350℉.
Topping
Coat bottom and halfway up the sides of a 9 inch, deep dish pie plate with 2 tablespoons of butter.
Evenly distribute all of the brown sugar in the bottom of the pie plate and press down to create what looks like a "crust."
Add the other 2 tablespoons of butter in little pats evenly over the top of the brown sugar.
Cut the pineapple slices in half. Start in the center of the pie plate and arrange the pineapple in a spiral over the sugar and butter pats. When finished, firmly press the pineapple down into the sugar as far as you can to ensure your pineapple design shows up on the top of your cake. Set pie plate aside.
Cake Batter
Using your stand mixer or hand mixer, cream the butter and sugar. Mix in eggs and vanilla.
In a separate bowl, whisk together to flour, baking powder, baking soda and salt. On low speed, mix this dry ingredient mixture a little at a time into the wet ingredients-- mixing each time just until ingredients are incorporated then adding a little more until all of the dry ingredients have been added. Don't overmix.Batter will be thick like cooke dough.
Add milk, crushed crushed pineapple WITH juice and sour cream to the empty bowl used to mix the dry ingredients. Whisk together then add to the thick cake batter. Mix on low just enough to incorporate. Then use a rubber spatula to gently fold the ingredients together until evenly combined.Batter will look a lot like a banana bread batter.
Spoon batter over your pineapple design, using your spatula to evenly spread the batter to the edges.
Bake
Place in preheated oven to bake for 50-55 minutes. Place a piece of aluminum foil over the top of the cake for the last 5-10 minutes of baking time if cake starts to over brown. Cake is done when it springs back when lightly pressed in the center, and the center no longer jiggles. The cake might start to crack a little. That's ok, but don't over bake.
Allow cake to cool 20 minutes on a baking rack before turning cake out onto a serving plate or cake stand.
Turning Out The Cake
Gently run a knife between the edges of the cake and pie plate. Place your serving platter or cake stand upside down on top of the pie plate, then flip. Cake should release easily. (You can see it through the bottom of the pie plate.) If it needs any help in spots, gently tap the bottom of the pie plate over that spot. Lift pie plate up and away from cake, and you're done!
If any of the topping sticks, just remove it from the bottom of the pie plate and add it back to the top of the cake.
Video
Notes
A glass deep dish pie plate really is best for baking a homemade pineapple upside down cake because it makes the "flip" so easy, but you could bake it in a 2 inch deep, 9 inch round cake pan or in a cast iron skillet. A spring form pan is not a good idea. Your caramelized topping will leak out.
When making your topping, firmly press the pineapple slices down into the sugar as far as you can to ensure your pineapple design shows up on the top of your cake. Otherwise, it might be covered with caramelized brown sugar.
Don't forget to pat the pineapple slices dry with a paper towel after draining them. I lay mine out a 2 layers of paper towels then blot them with a 3rd. If you don't pat them dry, they could add too much liquid to your cake and make it mushy.
Before you add the milk, crushed pineapple and sour cream, the batter WILL BE VERY THICK like cookie dough. Don't quit here because you think you did it wrong. Adding the next ingredients will create that nice batter you're looking for. Just do the steps, and it will be delicious!
Don't skip the cooling time. All that lava-hot, melted brown sugar has to cool and set before you flip the cake.