Pineapple Upside Down Cake Doughnuts – transform the ultimate retro Pineapple Upside Down Cake into baked doughnuts, sweet bites of nostalgia!
Note: This post was originally published on April 4, 2013. The recipe has been updated from the archives with updated content and photographs, as well as improved kitchen notes and recipe annotation. I hope you enjoy this favorite from my kitchen.
Every so often I pull out a little black folder tucked in the bottom of my desk drawer. I take it to the couch or into my bed, and with the same sense of calm as reading a novel, I sift through the hodgepodge of papers…recipes…from my mother. Some are laminated index cards with her handwriting in blue ink, cleanly written. Some are torn scraps of paper, franticly scribbled, as though she were in a rush. I imagine her taking these notes as she watched The Frugal Gourmet or Julia or Martin Yan. Then there are the magazine clippings, the newspaper food sections, yellowed with age.
I stopped at one the other night. On one side, ads for the local grocer, where you could buy fillet mignon for $2.38 a pound and cucumbers were 5 for 49 cents. A rotisserie chicken was $1.99 each. Each. On the other side, were several recipes for Pineapple Upside Down Cake. There was a version from 1925, another from Dole, and another for the skillet.
It brought me back to her Pineapple Upside Down Cakes. She favored crushed pineapples over slices, and the cake itself always had a lovely crumb. I’ve often wondered which of these versions she liked best.
As I reminisced, I had a vision of Pineapple Upside Down Cake Doughnuts. The little canned slices seem to be begging for it, don’t you think?
I baked a batch yesterday, and was so excited I just had to share them right away. Between nostalgia and sweet euphoria, I couldn’t resist.
How to Make Pineapple Upside Down Cake Doughnuts
Ever since I first shared this recipe, it has become a family favorite. I like to think of these doughnuts as individual servings of the classic pineapple upside down cake!
A simple brown sugar butter mixture is melted on the stove and placed in the bottom of each doughnut well.
I like to take each pineapple ring and slice them in half into thinner rings — this is critical not just for fitting into the pan, but also to provide the right pineapple to cake ratio in each bite. Just use a knife to carefully slice them in half!
Spread the batter on top of the pineapples and bake! The hard part is allowing the bake doughnuts to cool just enough so that it pops out of the pan easily. They’re especially delicious when eaten still warm, or can be cooled to room temperature and then enjoyed. I highly recommend enjoying them freshly baked!
More Doughnut Recipes
Pineapple Upside Down Cake Doughnuts
- 1/4 cup butter
- 1 cup brown sugar
- 1 15-oz can sliced pineapple drained
- 1/2 cup unsalted butter
- 1/2 cup granulated sugar
- 1 large egg
- 1 1/2 cups all-purpose flour
- 2 1/4 teaspoons baking powder
- 1/4 teaspoons kosher salt
- 1/2 cup buttermilk
- 1/4 teaspoon vanilla extract
- Preheat the oven to 350°F.
- In a small saucepan, melt the butter over medium heat. Stir in the brown sugar until it is moist. Spread in the bottom of your doughnut pan.
- Sliced the drained pineapples in half into thinner rings. Place the rings in the doughnut pan and press into the brown sugar.
- In the bowl of an electric mixer, beat the butter until it is creamy. Add the sugar and continue beating until fluffy. Add the egg and beat until it is fully incorporated.
- In a separate bowl, whisk together the flour, baking powder and salt. In a measuring cup, stir in the vanilla into the buttermilk. Add the flour mixture in increments to the butter mixture, alternating with the milk. Beat until just combined.
- Fill the doughnut pan about 2/3 full. Bake for about 18-20 minutes or until golden brown. Gently remove the doughnuts from the pan by inverting onto a plate.
- Let it cool on a wire rack…or enjoy immediately.
- Canned pineapple rings need to be sliced in half into thinner rings — this is critical not just for fitting into the pan, but also to provide the right pineapple to cake ratio in each bite. Just use a knife to carefully slice them in half!
- Allowing the bake doughnuts for about 8 minutes, or until they easily pop out of the pan without breaking apart.
- The doughnuts are delicious when eaten still warm, or can be cooled to room temperature and then enjoyed.
- I highly recommend enjoying them freshly baked, but cooled doughnuts can be stored in an airtight container in the refrigerator for up to two days.