Brown Sugar and Rum Pineapple Upside Down Cake
This is a really delicious, extra homey, pineapple upside down cake.  I’ve made it many times and it always brings a happy smile to my face.  It differs from the traditional pineapple upside down cake in that it’s sweetened with brown sugar rather than white.  To me, this really gives it a homier, friendly quality.  It’s spiced with a nice amount of ginger which blends beautifully with the warm brown sugar.  Instead of being decorated with the standard maraschino cherries, it is donned with pecan halves.  I loved how they add a soft crunch to the cake.  Hubby and I loved them so much we were fighting to get the most pecans in our slices and maybe we went so far as to steal a few from the unsuspecting cake!  Then to make this baby even more wonderful, fresh slices of pineapple are soaked in dark rum before baking to give the cake a little extra pizzaz!  I like to serve it while it’s still warm.  It’s like a hug from Mom in a slice of cake!

Brown Sugar and Rum Pineapple Upside Down Cake


  • 5 Rings Fresh Pineapple Cut Into 1/2 Rings
  • 1/2 Cup Dark Rum
  • 6 Tablespoons Plus 1/2 Cup Unsalted Butter
  • 1 2/3 Cup Dark Brown Sugar Packed, Divided
  • 1/3 Cup Pecan Halves
  • 1 2/3 Cup All Purpose Flour
  • 1 Teaspoon Dried Ground Ginger
  • 1 Teaspoon Baking Powder
  • 1 Teaspoon Baking Soda
  • 1/2 Teaspoon Salt
  • 3 Egg Large
  • 1 Tablespoon Vanilla Extract
  • 1 Teaspoon Mild Flavored Molasses
  • 2/3 Cup Buttermilk Well Shaken


  1.  Preheat oven to 350 degrees.
  2.  Pour rum in a 10X14 pyrex baking dish. Place pineapple rings in rum and flip them to coat. Let stand for about 30 minutes at room temperature.
  3. Melt 6 tablespoons of butter in a 9 1/2 inch cast iron skillet over medium heat. Add 1 cup of the brown sugar and whisk until sugar dissolves and syrup boils, about 2 minutes.  Drain pineapple and arrange in skillet in a nice pattern.  Tuck pecan pieces into spaces.
  4. Whisk flour, ginger, baking powder, baking soda and salt in a medium bowl.
  5. Beat 1/2 cup butter and 2/3 cup brown sugar in a large bowl.  Beat in eggs, vanilla, and molasses.  Beat in flour mixture in 3 additions alternating with 2 additions of buttermilk.  Spoon batter over pineapple.
  6. Bake in preheated oven about 35-40 minutes or until a toothpick inserted in center of cake comes out clean.
  7. Allow cake to cool for about 5 minutes. Place a large plate over the cast iron pan and flip it over.  Cake should pop right out.  Be careful!  I don't think anything is hotter than cast iron!