The Best Pineapple Upside-Down Cake in the World: My Holiday Favorite to Share by Jared Harding Wilson

by Jared Harding Wilson

The holiday season is all about warmth, gathering with loved ones, and creating sweet memories around the table. Last week, during our Come, Follow Me scripture study group, I baked my absolute favorite pineapple upside-down cake to share with friends. There’s something magical about flipping that golden beauty out of the pan and revealing those caramelized pineapple rings and cherries—it’s like unveiling a little gift. We enjoyed it warm, with laughter and good conversation flowing, reminding us that the true reason for the season is Christ, whose birth we celebrate brings light and joy into our lives. Sharing food like this with friends strengthens bonds and points our hearts toward Him, the ultimate source of love and generosity.

This recipe starts with a Duncan Hines base (I love their Signature Pineapple Supreme Cake Mix for that extra tropical flavor), but I’ve tweaked it over the years to make it extra special. Even though I used a Pyrex glass pan this time, I highly recommend a large cast-iron skillet if you have one—it gives the best caramelization and that classic crispy edge.

Ingredients

For the topping:

•  1/2 cup (1 stick) butter, melted

•  1 cup packed brown sugar

•  1 (20 oz) can pineapple slices, drained (reserve juice if needed)

•  Maraschino cherries (or fresh if available—I prefer fresh for their natural sweetness, but Smith’s didn’t have any this time!)

For the cake:

•  1 package Duncan Hines Signature Pineapple Supreme Cake Mix (or similar moist yellow/pineapple mix)

•  1 (3.4 oz) package French vanilla instant pudding mix

•  4 large eggs

•  1 cup water (or reserved pineapple juice for extra flavor)

•  1/2 cup oil

For serving (my special touches):

•  Homemade whipped cream (heavy cream, granulated sugar, and vanilla—whipped fresh)

•  Vanilla ice cream

•  Ground cinnamon for dusting

Instructions

1.  Preheat your oven to 350°F.

2.  Melt the butter in your pan (cast-iron skillet preferred) over low heat or in the oven. Remove from heat and stir in the brown sugar until evenly spread.

3.  Arrange the pineapple slices in a single layer over the brown sugar mixture. Place a cherry in the center of each pineapple ring and in any gaps for that classic look.

4.  In a large bowl, combine the cake mix, pudding mix, eggs, water (or pineapple juice), and oil. Beat on low until moistened, then on medium for about 2 minutes until smooth.

5.  Carefully pour the batter over the pineapple topping.

6.  Bake for 40-50 minutes (time varies by pan—check with a toothpick; it should come out clean). Let cool in the pan for 10-15 minutes, then invert onto a serving plate. (Pro tip: Place the plate over the pan and flip confidently!)

My Tips for Making It Extra Special

•  Fresh pineapple: I carve my own from whole pineapples bought at Sam’s Club. They often sell them green, so plan ahead—buy a few days early to let them ripen perfectly. The fresh chunks or rings taste worlds better than canned!

•  Whipped cream: Skip the Cool Whip (it has that chemical aftertaste for me). Instead, whip heavy cream with a bit of granulated sugar and pure vanilla extract right before serving. Time it so it’s fresh and fluffy.

•  Cherries: Fresh are ideal, but maraschino work in a pinch—just pat them dry so they don’t bleed too much.

•  Serving hot: This cake is heavenly straight from the oven. Slice it warm, add a scoop of vanilla ice cream on the side, a generous dollop of homemade whipped cream, and a light sprinkle of cinnamon on top. The contrast of hot cake, cold ice cream, and warm caramel is pure bliss.

We polished off most of the cake that night with our study group, and the leftovers (if there are any!) are just as delicious the next day. It’s a simple dessert that feels festive and thoughtful, especially during Christmas.

In this season of giving, let’s remember to share not just food, but our time and testimonies with those around us. Christ came to bring us together—may your holidays be filled with that same sweet spirit.

What’s your go-to holiday dessert that you love sharing with friends or family? I’d love to hear in the comments!