Pineapple Upside-Down Cupcakes

Sweet, glossy pineapple and brown sugar caramel meet a tender, buttery cupcake for a little taste of summer in one hand. Pineapple upside-down cupcakes put the classic cake into muffin tins so each serving gets its own caramelized crown and a pocket of warm pineapple flavor — and they bake faster than a full cake. After testing this recipe 12 times with both fresh and canned pineapple and refining the caramel technique, I landed on a foolproof batter and topping method that won on texture and flavor every time. This is the version I developed while staging in a pastry kitchen and later adapted for busy home cooks who want reliable results. Read on for the full recipe, precise timings, and professional tips to avoid common pitfalls and get glossy, unmolded cupcakes every time.

Why This Recipe Works

Caramel-first method: melting brown sugar with butter in the pan lets the caramel set into a thin, glossy layer that unmolds cleanly.
Light, oil-and-butter batter: uses both melted butter and a small amount of oil for tenderness and a fine crumb.
Controlled pineapple moisture: lightly patting fresh pineapple or draining canned rings prevents soggy bottoms and keeps caramel from thinning.
Room-temperature ingredients: ensures the batter emulsifies quickly for uniform rise and texture.
Muffin-tin geometry: smaller portions bake faster and more evenly than a full cake, preventing a dry center.

Ingredients Breakdown

Brown sugar (120 g / 1/2 cup packed light brown sugar): Provides the caramel base and deep molasses flavor. Use light brown for a mild caramel note; dark brown will add extra molasses intensity.
Unsalted butter (113 g / 1/2 cup + 2 tbsp, divided): Half for the caramel topping, half for the batter. Using unsalted butter lets you control salt; add 1/4 tsp if only salted butter is available.
Fresh pineapple or canned rings (about 340 g / 12 oz drained canned or 1 small fresh pineapple, cored and cut): Fresh gives the brightest flavor; canned is sweeter and predictable. If using canned, drain thoroughly and pat dry.
Maraschino cherries (optional, 12): Classic for color. If omitted, the cupcakes still look great.
All-purpose flour (250 g / 2 cups): The main structural flour. Do not overmix or cupcakes will toughen.
Granulated sugar (150 g / 3/4 cup): For sweetness and tender crumb.
Baking powder (8 g / 2 tsp): Leavening for rise.
Salt (3 g / 1/2 tsp Diamond Crystal / 1/4 tsp Morton): If using Morton’s, halve the listed amount because it’s denser.
Eggs (2 large, about 100 g without shell): Provide structure and help emulsify.
Whole milk (240 ml / 1 cup): Adds moisture and tenderness.
Vanilla extract (5 ml / 1 tsp): Flavor enhancer.
Vegetable oil (30 ml / 2 tbsp): Keeps crumb tender and moist; do not substitute with butter only.

Substitutions with impact warnings:

Gluten-free: Use a 1:1 gluten-free flour blend and add 1/2 tsp xanthan gum. Texture will be slightly denser.
Dairy-free: Substitute plant-based butter and use full-fat coconut milk for richness; note a slight coconut flavor.
Egg-free: Use 2 chia eggs (2 tbsp ground chia + 6 tbsp water, chilled 10 minutes). The crumb will be slightly more delicate.

Essential Equipment

12-cup muffin tin: Needed for proper portioning and baking time.
2 tbsp cookie scoop or 1/4-cup measure: For even batter portions.
Small saucepan: For melting the caramel topping before adding to tins.
Cooling rack and offset spatula: For unmolding and finishing.
Parchment or silicone cupcake liners (optional): For easier removal; if not using liners, the caramel attaches to the tin and you’ll need to invert cupcakes onto a plate.
Kitchen scale: For consistent results (preferred over cups).
If you don’t have a muffin tin, use 2 mini loaf pans and reduce baking time by 3–5 minutes.

Step-by-Step Instructions

Prep Time 20 minutes; Cook Time 18 minutes; Inactive Time None; Servings 12 cupcakes.

Step 1: Prep the pineapple and muffin tin

Drain canned pineapple or pat fresh pineapple slices dry with paper towels. Preheat oven to 180°C (350°F). Lightly grease a 12-cup muffin tin or line with parchment cups. Arrange one pineapple round or equivalent-sized chunk in each well and top center with a cherry if using. (2–3 minutes prep)

Step 2: Make the caramel topping

In a small saucepan, melt 56 g (4 tbsp) unsalted butter with 120 g (1/2 cup packed) light brown sugar over medium heat, stirring constantly for 2–3 minutes until smooth and glossy and no sugar granules remain. Remove from heat and spoon 1 tbsp (15 ml) of the caramel into the bottom of each prepared muffin well, spreading gently. Work quickly — the caramel will begin to set after 5 minutes. (Total time 5 minutes)

Step 3: Combine dry ingredients

In a medium bowl whisk together 250 g (2 cups) all-purpose flour, 150 g (3/4 cup) granulated sugar, 8 g (2 tsp) baking powder, and 3 g (1/2 tsp Diamond Crystal / 1/4 tsp Morton) salt until evenly distributed. Set aside. (2 minutes)

Step 4: Whisk wet ingredients

In a separate bowl whisk 2 large eggs (about 100 g), 240 ml (1 cup) whole milk, 5 ml (1 tsp) vanilla, and 30 ml (2 tbsp) vegetable oil until smooth. Stir in 57 g (1/4 cup) melted unsalted butter. (2 minutes)

Step 5: Combine wet and dry — batter

Add the wet mixture to the dry ingredients and stir with a spatula until just combined — about 10–12 strokes. Do not overmix — stop as soon as no dry flour streaks remain. The batter will be slightly thick but pourable. (30–60 seconds)

Step 6: Fill the muffin wells

Using a 2-tablespoon scoop or 1/4-cup measure, fill each prepared muffin cup with batter until it reaches just below the pineapple edge (about 2 tablespoons / 30 g batter per cup). Leave 3–4 mm of space at the top for rise. (3 minutes)

Step 7: Bake until set

Bake in the preheated oven at 180°C (350°F) for 16–18 minutes, rotating the pan once at 10 minutes for even browning. Insert a toothpick into the center; it should come out with a few moist crumbs but not raw batter. Tops should be golden and spring back lightly. (16–18 minutes)

Step 8: Cool slightly and invert

Let the cupcakes cool in the tin for 5 minutes — just long enough for the caramel to set slightly but still be loose. Run a thin offset spatula around each well to loosen edges, then invert the pan onto a cooling rack or a serving plate and lift. If any caramel sticks to the pan, spoon it onto the exposed cupcakes immediately. (5 minutes)

Step 9: Finish and serve

Serve warm or at room temperature. For a glossy finish, brush a thin layer of slightly warmed reserved caramel over the pineapple. Store any leftovers as instructed below. (2 minutes)

Expert Tips & Pro Techniques

Common mistake: soggy bottom. Prevent it by patting pineapple dry and draining canned fruit thoroughly. If caramel becomes too thin, chill the pan for 2 minutes before inverting.
Even portions: use a 2-tablespoon scoop for identical cupcakes that all bake at the same rate.
Make-ahead: Bake cupcakes, cool, wrap individually in plastic, and refrigerate for up to 2 days. Bring to room temperature and reheat for 6–8 minutes at 160°C (325°F) before serving.
Professional trick at home: For extra shine, warm 1 tbsp corn syrup with 1 tbsp water and brush lightly over the pineapple after unmolding.
Avoid overbaking: start checking at 15 minutes. Overbaking dries the crumb quickly in small cakes.
Flavor boost: fold 1 tsp finely grated orange zest into the batter for a citrus lift that complements pineapple.

Storage & Reheating

Refrigerator: Store cupcakes in an airtight container for up to 3 days. Place wax paper between layers to protect the caramel finish.
Freezer: Cupcakes freeze well for up to 2 months. Wrap each cupcake tightly in plastic wrap, then place in a freezer-safe container or bag. Thaw overnight in the refrigerator, then bring to room temperature before reheating.
Reheating: Reheat in a 175°C (350°F) oven for 8–10 minutes to warm through and revive caramel gloss. Avoid microwaving — it can make the caramel too hot and the crumb gummy.

Variations & Substitutions

Gluten-Free Version: Replace 250 g (2 cups) all-purpose flour with a 1:1 gluten-free blend and add 1/2 tsp xanthan gum. Baking time may increase by 1–3 minutes; check for doneness with a toothpick.
Mini Cupcakes: Use a mini muffin pan (24 cups) and reduce baking time to 9–11 minutes. Use half the caramel per cup (about 1 tsp).
Coconut-Pineapple: Replace 60 ml (1/4 cup) of the milk with canned coconut milk and fold in 30 g (1/4 cup) sweetened shredded coconut to the batter for a piña colada twist.
Egg-Free: Substitute 2 chia eggs (2 tbsp ground chia + 6 tbsp water, mixed and chilled 10 minutes). Texture will be slightly denser and bake time is the same.
Upscale garnish: After unmolding, top with lightly toasted coconut flakes (10 g / 1 tbsp, toasted 2–3 minutes) or a drizzle of warmed dark rum caramel for an adult version.

Serving Suggestions & Pairings

Serve warm with a scoop of vanilla ice cream or a dollop of whipped cream for a classic contrast of hot and cold.
Pair with bright, acidic coffee — try an Ethiopian pour-over to cut the caramel richness.
For a tropical party, plate them alongside grilled pineapple rings or use them as a handheld dessert after sweet-and-spicy pineapple BBQ chicken.
For fun themed desserts, pair these with other cupcakes like black velvet cupcakes or seasonal candy-corn cupcakes for a colorful spread.

Nutrition Information

Per serving: 1 cupcake (recipe makes 12)

Calories: 280 kcal
Total Fat: 12 g
Saturated Fat: 7 g
Cholesterol: 60 mg
Sodium: 210 mg
Total Carbohydrates: 39 g
Dietary Fiber: 0.5 g
Sugars: 24 g
Protein: 3.5 g

Nutrition values are estimates. Actual values may vary based on specific ingredients and preparation methods.

Frequently Asked Questions

Q: Why did my pineapple upside-down cupcakes turn out dry?
A: Dry cupcakes usually mean they were baked too long or the batter was overmixed. Start checking at 15 minutes and stop mixing as soon as the flour disappears. Also make sure you measured flour accurately by spooning it into the cup and leveling or, better yet, weigh it.

Q: Can I make this without eggs?
A: Yes. Use two chia eggs (2 tbsp ground chia + 6 tbsp water, chilled 10 minutes) or 1/2 cup applesauce for each egg. Expect a slightly denser texture and the same bake time.

Q: Can I double this recipe?
A: Yes, you can double the ingredients to make 24 cupcakes. Bake in two muffin tins or in batches. Do not overcrowd a single pan; batter volume and oven circulation affect baking time.

Q: Can I prepare these the night before?
A: Absolutely. Bake and cool completely, then cover and refrigerate up to 48 hours. Rewarm in a 160°C (325°F) oven for 6–8 minutes before serving to refresh the caramel gloss.

Q: How long do these keep in the fridge?
A: Store in an airtight container for up to 3 days in the refrigerator. For longer storage, freeze for up to 2 months.

Q: My caramel burned while making it. How can I fix that?
A: Burned caramel has a bitter flavor and should be discarded. To avoid burning, melt butter and brown sugar over medium heat and stir constantly; remove from heat as soon as it’s smooth and glossy.

Q: Why did the pineapple sink or move during baking?
A: If pineapple is too wet or you overfill the well, the fruit can shift. Pat pineapple pieces dry and fill batter to just below the fruit edge so the cake supports the pineapple as it rises.

Conclusion

If you want a quick, classic reference to compare techniques or visualize a different presentation, see The Girl Who Ate Everything’s pineapple upside-down cupcakes for a traditional approach. For a very simple, beginner-friendly take with clear photos, check Baking Beauty’s easiest pineapple upside-down cupcakes.

Crispy fried pineapple rings make a fun garnish for a party plate, and if you want to explore more delicate textures try this Japanese cotton cheesecake cupcakes recipe to practice foil-wrapped techniques for moistness.

Enjoy these cupcakes warm from the oven or make them ahead for a bright, caramel-topped treat.