Though communication is probably one of the top best things in my relationship with my boyfriend, he’s not great about disclosing his deepest food desires. So, when he finally mentioned seeing pineapple rum upside-down cupcakes on r/foodporn AND paired it with a story about his stepmom’s baking, I knew what needed doing.
Despite my resolve, I had never made a pineapple upside-down cake before and something about it made me nervous. (Maybe all the sticky-gooeyness and the potential for it to permanently adhere to my bakeware?)
A quick Googling of techniques and tips helped alleviate my fears and in the end, the cake was super moist, flavorful, AND pretty. Phew.
The recipe is an amalgamation of several other recipes I’ve used over the years, with many tweaks added in thanks to the horrifically unforgiving process of trial and error (e.g. many-a-failed dish right before a major dinner party) and some internet research.
Note: I call this “easy” pineapple upside-down rum cake because I’m a cheater who uses box cake mix as a base. I find this lends itself to a more reliable baking experience. Purists (*cough*Brie*cough*) may disagree.
Above and beyond your usual baking equipment, I suggest having the following on-hand for this recipe:
- 9-inch springform cake pan
- Flat spatula (for unsticking the pretty pineapple topping from the cake pan)
- Thin pokey thing (I used a single chopstick)
- 1 box yellow cake mix
- 1 box instant vanilla pudding mix
- 4 eggs
- ½ cup vegetable oil
- ¼ cup water
- 1 cup dark rum
- 1 cup white sugar
- Non-stick cooking spray
- ¼ cup all purpose flour
- 1 cup brown sugar
- ½ cup butter softened, plus ½ cup melted
- 1 20-ounce can of pineapple rings
- 1 small jar of maraschino cherries
- Preheat the oven to 325 degrees Fahrenheit.
- Apply non-stick cooking spray to 9" springform cake pan, then coat pan with flour.
- Sprinkle brown sugar evenly over the bottom of the cake pan.
- Slowly drizzle ½ cup of melted butter evenly over the brown sugar.
- Refer to figure 1 for the pineapple and maraschino cherry layout. Carefully arrange the pineapple slices and cherries on top of the brown sugar and butter layer in the cake pan to match.
- Set aside the remaining pineapple juice for later and reserve remaining pineapple slices and cherries for snacking (or another cake!).
- In a large bowl, combine cake mix, pudding mix, eggs, ½ cup pineapple juice (leftover from the can), ½ cup vegetable oil, and ½ cup rum. Mix well.
- Pour batter over pineapple slices & cherries in the cake pan.
- Bake in the preheated oven for 60 minutes or until a toothpick inserted into the center comes out clean. Let cool for 10-15 minutes.
- In a sauce pan combine remaining butter, ¼ cup water, and 1 cup sugar. Bring to a boil over medium heat and continue to boil for 5 minutes, stirring constantly. Pour in ½ cup rum and stir for 1 additional minute. Remove from heat.
- Poke several holes in the base of the cooled cake. Slowly pour ¾ of the rum and sugar mixture onto the cake and allow it to soak in. If it is slow to absorb, you may need to poke additional holes into the cake.
- Flip the cake pan over onto a serving platter. Release the springs and remove the outer metal ring.
- Very carefully use the flat spatula to gently pry the top of the cake pan away from the sticky cake top. Go slowly.
- Pour remaining rum and sugar mixture over the top of the cake.
- You are now the proud owner of a very pretty pineapple upside-down rum cake.
She lives in the Bay Area and cites her diverse background as her biggest influence: her visual artist mom is half-Chinese, half-Greek, and from Hawai’i; her film-loving, world-music curating dad is from Montana; and she lived in both California and Montana while growing up. She loves at least a little bit about virtually everything (Pokémon Snap included) and aims to be a Jane of all trades. By day Cat is a multiple-hat-wearing media person.
She is also allergic to felines.