Name: MLK Day Healthy Pineapple Upside Down Cake Recipe
Prep time: 20 min
Cook time: 30 min
Total time: 50 min
Cuisine: American
Ingredients: 2 Tbsp coconut oil; ¼ cup coconut sugar; 7 fresh pineapple rings (about 1 medium pineapple, peeled, cored, and sliced ½-inch thick); 7 frozen dark sweet cherries, thawed and patted dry; 1½ cups white whole-wheat flour; 1 tsp baking powder; ½ tsp baking soda; ½ tsp ground cinnamon; ¼ tsp fine sea salt; ½ cup plain 2% Greek yogurt; ⅓ cup pure maple syrup; ¼ cup pineapple juice (from fresh pineapple or canned 100% juice, drained); 2 large eggs; 2 Tbsp melted coconut oil; 1½ tsp vanilla extract

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Introduction

This healthy twist on the classic Pineapple Upside Down Cake brings tropical flavors with wholesome ingredients. Using fresh pineapple, whole-wheat flour, and natural sweeteners, it’s a delightful dessert perfect for celebrations or a cozy treat.

A round cake sits on a wooden board dusted with white powder. The cake has two main layers: a thick, light yellow base layer with a crumbly texture, and a glossy yellow top layer. On top, there are seven large, circular slices of grilled pineapple placed evenly, each with a bright red cherry in the center. More cherries are scattered around the edges of the cake between the pineapple slices. The cake and board rest on a white marbled surface. photo taken with an iphone --ar 4:5 --v 7

Ingredients

2 Tbsp coconut oil (for fruit layer)
¼ cup coconut sugar
7 fresh pineapple rings (½-inch thick)
7 frozen dark sweet cherries, thawed
1½ cups white whole-wheat flour
1 tsp baking powder
½ tsp baking soda
½ tsp ground cinnamon
¼ tsp fine sea salt
½ cup plain 2% Greek yogurt
⅓ cup pure maple syrup
¼ cup pineapple juice
2 large eggs
2 Tbsp melted coconut oil
1½ tsp vanilla extract

Instructions

Step 1: Preheat your oven to 350 °F (175 °C) and lightly grease a 10-inch cast-iron skillet.
Step 2: Melt 2 tablespoons of coconut oil in the skillet over medium heat. Sprinkle the coconut sugar evenly, then arrange the pineapple rings in a single layer. Place one cherry in the center of each ring. Let it sizzle for 3 minutes to start caramelizing the fruit.
Step 3: In a large bowl, whisk together the whole-wheat flour, baking powder, baking soda, cinnamon, and sea salt.
Step 4: In a separate container, combine the Greek yogurt, maple syrup, pineapple juice, eggs, melted coconut oil, and vanilla extract. Whisk until smooth.
Step 5: Pour the wet mixture into the dry ingredients and gently fold with a spatula until just combined with no streaks of flour remaining. Avoid over-mixing.
Step 6: Spoon the batter evenly over the caramelized pineapple and cherries in the skillet. Gently spread to the edges, then tap the skillet once on a towel-covered counter to release air bubbles.
Step 7: Bake for 28 to 32 minutes, until the center springs back lightly and a toothpick inserted comes out with a few moist crumbs.
Step 8: Let the cake cool for 8 minutes to prevent caramel hardening. Run a thin knife around the edges, place a heatproof plate on top, and invert in one confident motion. Lift the skillet slowly and reposition any fruit that sticks. Serve warm or at room temperature.

Tips & Variations

If you don’t have a cast-iron skillet, use a 9-inch cake pan set on a preheated sheet tray to help caramelize the fruit.
Pat pineapple slices dry with paper towels to avoid soggy bottoms and help the caramel adhere better.
For dairy-free, replace Greek yogurt with coconut yogurt and swap each egg with a flax egg (1 Tbsp flaxseed meal + 3 Tbsp water).
Add ¼ tsp cardamom to the dry ingredients for a floral touch that complements the pineapple beautifully.
Try folding ½ cup finely grated carrot into the batter for extra color and nutrition.
For a gluten-free option, substitute white whole-wheat flour with a 1:1 gluten-free baking blend including xanthan gum.
To make mini cakes, divide batter among 12 muffin cups lined with parchment and bake for 18 minutes.

Storage

Cover leftovers with an inverted bowl or beeswax wrap and refrigerate for up to 4 days. The fruit layer will stay glossy but the cake will firm up—bring slices to room temperature 30 minutes before serving or warm in the microwave for 10 seconds to regain softness. To freeze, cool completely and cut into wedges. Wrap each slice in parchment and foil, freeze up to 2 months, then thaw overnight in the refrigerator. Refresh in a 300 °F oven for 8 minutes before serving.

How to Serve

A round pineapple upside-down cake with one visible thick brown crust layer at the bottom, topped by a yellow moist cake layer. On top, seven large, golden-yellow pineapple rings with light grill marks form a circular layer, each ring holding a shiny red cherry in the center. Additional whole cherries are placed between the pineapple rings on the cake. The cake sits on a round wooden board dusted with white powdered sugar, all set on a white marbled surface. The image captures close-up details of the glossy pineapple and cherries. Photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use canned pineapple in syrup?

It’s best to use fresh pineapple or canned pineapple packed in 100% juice, drained well. Avoid syrup-packed pineapple as the extra sugar can cause sogginess and overpower the caramel flavor.

My fruit stuck—what happened?

Make sure to melt the coconut oil and sprinkle the coconut sugar evenly before adding the pineapple. Also, allow the fruit to sizzle for a few minutes to form caramel. If the fruit sticks when inverting, gently nudge it back onto the cake with a knife.