Pineapple Upside Down Cake

Pineapple Upside Down Cake. Spiked with rum. Studded with Cointreau-soaked raisins. Blanketed by sticky caramel.

So good. So sweet. I can’t even write in full sentences.

I’ve never made Pineapple Upside Down Cake before. But there’s always a first for everything, and my first attempt was for someone very special: my mom.

When my mom‘s birthday rolled around a few days ago, she and my dad were here in Boston, and I thought I could grab the opportunity to bake some elaborate cake for us to celebrate. I grilled her for the types of cakes she might like, but she didn’t want any fancy, elaborate cakes. She wanted something simple, something unfussy, something that reminds her of her own mom: Pineapple Upside Down Cake.

My mom said that my grandmother used to bake the best Pineapple Upside Down Cakes. Sweet, moist, with syrupy caramel dripping down the sides. She said that my grandmother used to have her friends over and they would have baking sessions, and this upside down cake was one of her specialties. I never met my grandmother because she passed away before I was born, but my mom says that she and I are alike in many ways. (And if I had enough room in my apartment, I would love to have my friends come over for baking sessions, too.) I think she would’ve approved of this cake I made – I took a classic recipe but added my own touches: pineapple in the actual cake, orange liqueur-soaked raisins, some rum instead of milk, glazed pecans, and double the caramel.

Oh yes.

Doubling the caramel created some (easy-to-solve) problems: the caramel topping, which while baking was at the bottom of the cake pan, ended up oozing out and dripping on the oven floor, creating a lot of smoke, some unsettling sizzling sounds, and the (welcome) scent of burnt sugar. But I simply turned off the oven, cleaned up the dripped caramel with a paper towel, then placed the cake pan on top of a cookie sheet covered in foil – so that if it drips down again, it’s just going to drip on the foil, making for easy clean-up. And no, the caramel on the cake didn’t burn.

In fact, it turned into a sticky, gooey, caramelized coating that absorbed nicely onto the top and sides of the cake. And after thoroughly cooling, some parts of the caramel turned slightly chewy and crunchy, melding sweetly with the glazed pecans. It was a great birthday cake. I loved it. My sweet-toothed dad loved it. And best of all, the birthday celebrant enjoyed every caramely bite.

Pineapple Upside Down Cake


1 1/3 cups all-purpose flour
3/4 cup sugar
2 teaspoons baking powder
1/2 teaspoon salt
1/4 cup vegetable oil
1/2 cup milk (I used 1%)
1/4 cup dark rum
1 teaspoon vanilla
1 egg
grated rind from 1 lime
1 tablespoon fresh lime juice
1/4 cup raisins
1/4 cup orange liqueur
1/2 cup butter (1 stick), plus a little more for buttering the baking pan
1 cup dark brown sugar
1 20-ounce can pineapple slices
1/4 cup pecans (I used glazed pecans from Q's Nuts)


  1. Soak raisins in orange liqueur for 30 minutes.
  2. Preheat the oven to 350 degrees F.
  3. Make the cake. In a mixing bowl, sift together the flour, sugar, baking powder, and salt. Add the oil and milk to the bowl and whisk together until well incorporated. Add the rum, vanilla, egg, lime rind, and lime juice, blending just until well combined. Fold in raisins.
  4. Make the caramel. Place the brown sugar and butter in a saucepan on medium heat until sugar dissolves and the mixture is bubbly, stirring lightly.
  5. Butter a 9- or 10-inch cake pan. Pour caramel in. Arrange the pineapple slices and pecans on top. Take the remaining pineapple slices, chop coarsely and fold into the cake batter. Pour the batter evenly over the top and bake for 45 minutes.
  6. Remove from the oven and cool the cake in the pan for 10 minutes. Turn the cake out onto a circular platter.

recipe adapted from Martha Stewart

There is a special joy that comes with having the chance to bake a cake for my mom. And seeing her and my dad enjoy the cake makes it even sweeter.

This cake is for the grandmother I never met and for the mother I am so lucky to have. Happy birthday, Mommy!


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