pineapple upside down sheet cake

Fully Loaded Pineapple Upside-down Cake

Mom and Nana were great bakers and my Mom could turn out the best pie crust on earth blindfolded, but we seemed to have more cakes in our Coal Region kitchen repertoire than pies. My Dad was a great fan of cakes.

I highly suspect the portability factor of many cakes — especially some of Pop’s favorites like Brown Stone Front Cake — afforded them honored spots on his “must-have” list.

All throughout my Pop’s working life — from days in the coal mines to hauling coal in his tractor/trailer to cities on the East Coast to several years as a heavy equipment operator — he carried the ubiquitous “hump-top” lunch box. Guaranteed to be found in that lunch box was a Thermos filled with hot coffee, 2 sandwiches and either a pack of Tastykake Butterscotch or Jelly-filled Krimpets (which my Mom bought by the box-full) or a generously cut piece of the cakes Mom lovingly baked nearly every week.

Tastykake Vintage Sign

My Dad’s indulgence in cake was severely curtailed when he was diagnosed with Type 2 diabetes a few years before he passed away, but at holidays or on special occasions, Pop indulged in a small taste of his favorites. In order not to tempt him in those final years, the baking in our house was reduced. On occasion, lucky friends and family found themselves gifted with a variety of excess baked goods because, try as Mom and I might, the Coalcracker in us just couldn’t come to terms with cutting recipes in half!

Turns out my late husband, James, loved cake, too. I learned this when he polished off the multi-tiered blackberry/Chambord filled vanilla “practice” cake I made and decorated in preparation for our wedding September 1997. James had a huge sweet tooth, actually. I often called him a “sugar fiend”, a label he didn’t shy away from.

The first time I made a pineapple upside down cake for James, I did it in the traditional style, laying out whole pineapple rings in the bottom of the pan and inserting Maraschino cherries into the inside of the ring. James was anxious for it to cool and lopped off a hefty piece. Awhile later, I happened to pass him sitting at the dining room table, a chunk of yet-to-be-eaten cake on his plate. He looked up forlornly and lamented, “It’s good, but now it’s naked…”

Upon closer look, I realized he had eaten the pineapple and cherry but now had only cake left. He sounded like a disappointed little boy at Christmas who liked the gift he got but it wasn’t really what he wanted and was doing his best to be polite about the situation. I grinned, hugged him, and whispered in his ear, “Next time, I’ll be sure to fix that.”

The solution

For over two decades now I have been making what we jokingly referred to as a “fully-loaded” pineapple upside down cake — fully loaded because no “naked” spaces remain on top — you get luscious, gooey goodness in every bite. I no longer use pineapple rings, but use pineapple tidbits; these are a cut smaller than “chunks” but larger than “crushed”. Dole brand tidbits can be found in many supermarkets. And since James, like my Pop, had a habit of stealing and eating draining Maraschino cherries, I started buying a large jar giving me plenty with which to stud the bottom/once-flipped “top” of the cake.

We liked pineapple cake to taste like pineapple; I use the drained pineapple juice in place of water in the ingredients for the cake itself, and I always use a pineapple-flavored cake mix. Salted butter in the “gooey” portion enhances the flavors and dark brown sugar rounds out the goodness. I’m positive my Pop would have given his full approval to this version.

Fully Loaded Pineapple Upside-down Cake

Recipe by Lori Fogg, A Coalcracker In The KitchenCourse: DessertCuisine: GeneralDifficulty: Intermediate


  • Topping/bottom
  • 1/2 cup (1 stick) salted butter, melted

  • 1 cup packed dark brown sugar

  • 1 (20 ounce) can pineapple tidbits in its own juice, well drained, reserve 1 cup liquid (add water to make 1 cup, if needed)

  • 18 to 20 Maraschino cherries

  • Cake

  • Cake
  • 1 package (15.25 ounces) Duncan Hines® Signature® Pineapple Supreme Cake Mix

  • 1 cup reserved pineapple juice (and enough water to make 1 cup if needed)

  • 1/3 cup vegetable oil

  • 3 large eggs


  • Preheat the oven to 350F degrees. Line an appropriately sized baking sheet or tray (large enough to hold the baked cake) with parchment or foil. (I use a cookie sheet and wrap it in foil.) Set aside for later.
  • Lightly spray a 13 x 9-inch pan with cooking spray. Pour melted butter in pan and sprinkle evenly with brown sugar.
  • Arrange pineapple tidbits and cherries on top of brown sugar fully covering the surface. (Press the cherries through the pineapple/brown sugar so they touch the bottom of the pan).
  • Combine cake mix with pineapple juice, oil and eggs in large bowl. Beat with an electric mixer at low for 30 seconds; then beat at medium speed for 2 minutes. Pour over pineapple and cherries in pan. Spread evenly with offset spatula if necessary.
  • Bake for 35 to 40 minutes or until a toothpick inserted in center comes out clean. Cool cake in pan on wire rack for 5 minutes. Run the knife around the sides of pan to loosen cake. Invert cake onto a foil or parchment-lined serving or baking sheet of the appropriate size to hold the cake. Drizzle any remaining sauce or fruits over cake. Serve warm or cool.