Now that I’ve introduced you to Filipino roadside fruit stands overflowing with pineapples and produce and I’ve showed you how to cut a pineapple fresh from the farm, I’m going to share with you how to make one of my all-time favorites: pineapple upside-down cake.  Thomas Keller has an amazingly simple recipe that uses fresh pineapples. Canned pineapples will work, too but fresh ones make it more elegant.

Making pineapple upside-down cake starts with making a “pan schmear” of butter and brown sugar and then pouring the cake batter over pineapple slices arranged in overlapping rings.

Pineapple Upside-Down Cake Recipe
Recipe adapted from Thomas Keller’s Ad Hoc at Home

For the pan schmear

8 Tbsp (1stick, 4 oz) unsalted butter, at room temperature
1-1/2 Tbsp honey
1/2 tsp dark rum
1 cup packed light brown sugar
1/4 tsp vanilla paste or pure vanilla extract
Kosher salt

Preheat the oven to 350 degrees F.

In the bowl of a stand mixer fitted with the paddle, combine the butter, honey, rum, brown sugar, and vanilla and beat until smooth and well blended. Spread half a cup of schmear over the bottom of a 9-inch silicone cake pan. A metal cake pan will work as well, in fact, this is what we used here but make sure to grease the pan with butter before using it.

Here’s an important note. The recipe makes more schmear than necessary for a single cake but Keller points out in his book that it is difficult to make less. We tried cutting the recipe in half but had a challenging time beating it in the stand mixer. It was doable but a bit hard. When baking just a single cake, note that the schmear will keep for a couple of weeks in the fridge or it can be frozen for future use.

Cut the peeled pineapple lengthwise into quarters.  Here is a link to learn how to peel and cut a fresh pineapple.

How to make pineapple upside-down cake

Cut off the core from each section and then cut each piece crosswise into 1/8-inch-thick slices.

How to make pineapple upside-down cake

Starting at the perimeter of the pan, arrange the pineapple slices, with the curved side facing out, and form an overlapping ring as shown in the photo. Make a second ring inside the first one, overlapping the pineapple slices in the opposite direction, working toward the center of the pan.

How to make pineapple upside-down cake

For the cake

1-1/3 cups cake flour
2 tsp baking powder
8 Tbsp (1 stick, 4 oz) unsalted butter, at room temperature
1/2 cup plus 2 Tbsp granulated sugar
1/2 tsp vanilla paste or pure vanilla extract
2 large eggs
1 Tbsp plus 1 tsp milk

Sift the flour and baking powder together and set aside.

Put the butter and sugar in the bowl of a stand mixer fitted with the paddle and mix on low speed to combine, then beat on medium speed for about three minutes, until light and creamy. Stop to scrape down the sides of the mixer when necessary and continue mixing. Mix in the vanilla. Add the eggs one at a time, beating until the first one is fully incorporated before adding the second and again, stop and scrape down the sides when necessary. Beat in the milk. Add the flour mixture in 3 batches, beating until well combined.

Put the batter into the cake pan and spread gently over the pineapple. Bake for 15 minutes. Rotate the pan for even browning and bake for another 20 to 25 minutes, until a toothpick inserted in the center of the cake comes out clean.

Let the cake in the pan cool on a cooling rack for 20 to 30 minutes. Run a knife around the edges of the cake, invert onto a serving platter, and serve warm.

Pineapple Upside-Down Cake

One final word. Be generous with the schmear, which is really the good stuff that makes the cake extra moist. Keller calls for 1/3 cup of pan schmear, I would go ahead and even put 1/2 cup of this buttery-sugary goodness.