Pineapple Upside Down Cake

Dad's birthday was celebrated at brunch time, so it seemed a little weird to make a traditional birthday cake. Combined with the slew of birthday and Valentines related treats, I was looking to make a bit of a lighter cake! Fruity desserts are healthier, right?? :-)

I debated between two recipes for this old classic. One was from old faithful Cooks Illustrated, while the other was from Chang's Flour Recipe Book. I went with the CI recipe since they used brown sugar in their caramel sauce, which sounded tastier. I'm sure both are wonderful, though. This sure was! My only advice would be to make this dish the same day you're serving it. Since I had a volunteer commitment the morning of my dads birthday brunch, I made the cake the day before. I think the refrigeration changed the consistency a bit, and next time I'll make this when I can serve or eat it immediately!

Ingredients:

Pineapple topping:
1 medium fresh pineapple, peeled and diced in small pieces
1 cup firmly packed light brown sugar
3 tablespoons unsalted butter
1/2 teaspoon vanilla

Cake:
1.5 cups flour - I used GF Better Batter!
1.5 teaspoons baking powder
8 tablespoons unsalted butter, softened
3/4 cup granulated sugar
1 teaspoon vanilla
2 eggs, room temperature
1 egg white, room temperature
1/3 cup whole milk

Grease one 9 inch round, 2 inch deep round cake pan with butter or nonstick cooking spray.

For the pineapple topping: combine the pineapple and brown sugar in a 10 inch skillet.

Cook over medium heat, stirring occasionally during the first five minutes, until pineapple is translucent and has a light brown hue, 15 - 18 minutes.

Empty the fruit and juices into a mesh strainer or colander set over a medium bowl. Return the juices to the skillet, leaving the pineapple in the strainer, returning the bowl underneath to catch additional juice.

Simmer juice over medium heat until thickened, 6 - 8 minutes.

Feel free to add more of the juice that collects in the bowl, but don't worry about all of it, especially if it gets added past the four minute mark as it won't have time to reduce. Off heat, add the butter and vanilla.

Whisk until butter melts and then add the mixture, which is now caramel, into the bottom of the 9 inch cake pan.

Preheat the oven to 350 degrees. Whisk flour, baking powder, and salt in a medium bowl and set aside.

In the bowl of a standing mixer with a paddle attachment, cream the butter and sugar at medium-high speed until mixture is light and fluffy, 3-4 minutes. Reduce speed to medium, add vanilla, and beat to combine the eggs, one at a time (ending with the egg white). Scrape down the sides of the bowl after each addition. Reduce speed to low, add one third of the flour mixture, and beat until mixed. Add one half the milk, and repeat with the remaining thirds of the flour mixture and half of the milk. Give the whole thing a final stir with the spatula. The batter will be thick!

Here are your three items:

Distribute the cooked pineapple in the cake pan in an even layer, gently pressing the pineapple into the caramel.

Spread the cake batter over the pineapple/caramel layer and tap the pan to release any air bubbles. Bake until the cake is golden brown and passes the toothpick test, 45 - 50 minutes. Cool for 10 minutes, not much longer so the caramel doesn't harden in the pan, and then place the inverted serving platter over the cake pan. Invert the cake pan and platter together, lift off cake pan. Your cake should be left behind!