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!


21 Responses to “Pineapple Upside Down Cake”

  1. #
    Emily @ A Cambridge Story posted September 15, 2012 at 8:57 am

    This looks AWESOMELY gooey!

  2. #
    Rhonda posted September 15, 2012 at 12:30 pm

    That looks so amazing. I love pineapple upside down cake, it combines so many wonderful flavors and textures. Have a wonderful weekend.

  3. #
    Sam @ TheSecondLunch posted September 15, 2012 at 1:07 pm

    I can’t help but thinking, how delicious would this be as ice cream? Well, minus the raisins. (Even the cointreau won’t make them taste any better for me, alas.)

  4. #
    Kathryn posted September 15, 2012 at 6:19 pm

    What a wonderful cake, I love your little touches!

  5. #
    Choc Chip Uru posted September 16, 2012 at 7:10 am

    You just take this cake to a whole new gorgeous level :D


  6. #
    grace posted September 16, 2012 at 5:13 pm

    raisins! seeing those in an upside-down cake is a first for me, but it’s a great touch. very nice cake!

  7. #
    Meghan posted September 17, 2012 at 8:24 am

    This looks delicious and reminds me that my mom makes an amazing peach upside down cake! I need to have her make it the next time I am home.

  8. #
    Michelle Collins posted September 17, 2012 at 2:35 pm

    You had me at caramel and rum.

  9. #
    Megan posted September 17, 2012 at 10:57 pm

    Looks gooey, decadent, and amazing. Your mom must have loved it!

  10. #
    Jenny @ BAKE posted September 18, 2012 at 8:35 am

    I was sold on the description alone but your photos are gorgeous too!

  11. #
    Carol @ Always Thyme to Cook posted September 18, 2012 at 9:42 am

    Gorgeous cake. All that delicious caramel with pineapple and pecans. So good!

  12. #
    bianca @ sweet dreaming posted September 18, 2012 at 10:32 am

    loooks delish!

  13. #
    Allie posted September 18, 2012 at 3:19 pm

    Pineapple upside down cake was my favorite to make as a kid! But it was definitely lacking in caramel and rum. I think I’d like this adult version even better ;D

  14. #
    Elizabeth posted September 18, 2012 at 7:31 pm

    I friggin LOVE pineapple upside down. It’s all about the caramel coating.

  15. #
    Sues posted September 18, 2012 at 8:02 pm

    This is beautiful and looks SO SO tasty!

  16. #
    Simply Life posted September 19, 2012 at 7:31 am

    oh what a sweet cake- I loved that last line on your post – so sweet :)

  17. #
    Shannon posted September 19, 2012 at 4:06 pm

    oh my my, this looks absolutely fantastic!! what a fantastic celebration for mom :)

  18. #
    OliePants posted September 21, 2012 at 11:48 am

    This is one of those cakes that I love but never have as often as I want. I have never made it – that needs to change!

    • #
      Bianca Garcia posted September 21, 2012 at 12:16 pm

      Yes, and it’s actually a pretty easy recipe too!

  19. #
    Taryn posted September 22, 2012 at 10:07 am

    I LOVE upside down cakes! I actually just saw a recipe for one in Bon Appetit this morning – I might make this tonight! Yum.

  20. #
    Samantha Angela posted October 3, 2012 at 3:44 pm

    This looks so amazing! I love pineapple upside down cake but I’ve never even made it before!

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