Gingerbread Pineapple Upside-Down Cake
Adapted from a recipe by Kathryn Pauline, from A Dish for All Seasons, published with permission by Chronicle Books. All rights belong to the publisher.
I don’t make pineapple upside-down cake often, but when I do, I want it darker and more grounded — molasses-heavy, gently spiced, and not overly sweet. This version leans into gingerbread: fresh ginger, cardamom, orange zest, and just enough cocoa to deepen everything without turning it into a chocolate cake.
The fruit softens into the brown sugar and butter, the cherries bleed slightly, and the cake stays tender and fragrant. It’s familiar, but not nostalgic for nostalgia’s sake — the kind of cake you cut into while it’s still warm, then quietly return to the next day.
Ingredients
Fruit Layer
• 4 Tbsp (55 g) unsalted butter, melted
• ½ cup (100 g) dark brown sugar
• 1 (15 oz / 425 g) can pineapple rings, drained and patted dry
• About 15 jarred Morello or maraschino cherries, drained (about 40 g)
Dry Ingredients (Cake)
• 1½ cups (195 g) all-purpose flour
• 2 Tbsp cocoa powder
• 1 Tbsp ground ginger
• 1 tsp ground cinnamon
• ½ tsp ground cardamom
• ½ tsp salt
• 1¼ tsp baking powder
• ¼ tsp baking soda
Wet Ingredients (Cake)
• 2 large eggs, at room temperature
• 4 Tbsp (55 g) unsalted butter, melted
• ½ cup (100 g) dark brown sugar
• ¼ cup (85 g) molasses
• ½ cup (120 g) buttermilk*
• 1 Tbsp freshly grated ginger
• 1 tsp orange zest, plus more for finishing
To finish:
• Confectioners’ sugar, for dusting
Method
Prepare the pan & fruit
Preheat the oven to 350°F (180°C). Butter a 9-inch (23 cm) round cake pan and line the base with a parchment round.
In a small bowl, whisk together the melted butter and brown sugar. Pour the mixture into the pan and spread it evenly. Arrange the pineapple rings in a single layer (break one if needed to fill the edges). Place a cherry in the center of each ring and tuck the remaining cherries into the gaps.
Make the batter
In a large bowl, sift together all the dry ingredients.
In another bowl, beat the eggs with the melted butter until smooth. Add the brown sugar, molasses, buttermilk, fresh ginger, and orange zest, and beat until well combined.
Pour the wet ingredients into the dry and gently fold just until no dry flour remains. Don’t overmix.
Bake
Carefully spoon the batter over the fruit and smooth the top. Bake for about 35 minutes, until a toothpick inserted into the center comes out clean.
Let the cake cool in the pan for 5–10 minutes, then run a knife around the edge and invert onto a serving plate. Allow it to cool for at least 30 minutes before slicing.
Just before serving, finish with a little extra orange zest and a light dusting of confectioners’ sugar.
Notes
• Buttermilk substitute: Mix ½ cup milk with 1½ tsp lemon juice or vinegar. Let stand for 5 minutes.
• Keeps well, covered, at room temperature for 2 days. The flavor deepens overnight.
• Lovely slightly warm, but even better the next day.
