This show-stopping retro pineapple upside down cake recipe is made with simple pantry staples, yet yields a moist and fluffy cake topped with gorgeous cherry-filled pineapple rings! Recipe includes a how-to video.
Pour melted butter into 9.5-10" pie plate or deep cake pan, make sure it entirely covers the bottom of the pan and use a spoon or spatula to grease the sides of the pan.
¼ cup salted butter
Sprinkle brown sugar evenly over butter mixture. Arrange pineapple slices over the bottom of the pan, slice leftover slices in half and arrange up the sides of the pan, as seen in photo.
½ cup brown sugar, 10 pineapple slices
Place cherries in center of pineapple rings and as desired in empty spaces. Set aside.
maraschino cherries
To prepare vanilla cake, beat butter and sugar in medium-sized bowl until creamy and well-combined.
½ cup unsalted butter, ¾ cup granulated sugar
Add eggs, beating one at a time until combined.
2 large eggs
Stir in vanilla extract.
1 teaspoon vanilla extract
In a separate bowl, whisk together flour, baking powder, and salt.
1 ½ cups all-purpose flour, 1 ½ teaspoons baking powder, ¼ teaspoon salt
Alternate adding flour and milk to the wet ingredients, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to overmix).
½ cup whole milk
Pour batter evenly over prepared cake pan over the pineapple/cherry layer.
Bake on 350F (175C) for 30 minutes. At the 30 minute mark, loosely cover with foil and continue to bake (still on 350F/175C) for another 15 minutes, until a toothpick inserted in the center comes out mostly clean with few crumbs (total cook time for cake will be 45 minutes).
Allow to cool for 10-15 minutes and then carefully invert cake onto serving platter (careful, it will still be very hot!).
Allow to cool before cutting and enjoying, but don't wait too long as this cake tastes wonderful (best!) warm from the oven!
Video
Notes
Milk
I use and recommend whole milk, but many readers have substituted lower-fat milk or almond milk with success. Some readers have substituted the milk in this recipe with pineapple juice, I think the difference in taste is negligible and prefer the texture of the cake when made with milk, but it can be done.
Gluten Free
Readers have commented that they have successfully made this recipe by using a 1:1 substitution of all-purpose gluten free cup4cup flour.
Serving & Storing
Pineapple upside-down cake tastes best fresh and doesn't keep as well as most layer cakes. However, if you wish to keep it, cover it with foil or plastic wrap or place in an airtight container and refrigerate for up to three days. You may also wrap tightly and freeze for several weeks.