Ingredients
Scale
- For the sugar cookie base:
- 1/2 cup unsalted butter, softened
- 1/2 cup granulated sugar
- 1/4 cup brown sugar
- 1 egg
- 1 tsp vanilla extract
- 1 1/2 cups all-purpose flour
- 1/2 tsp baking soda
- 1/4 tsp salt
- For the topping:
- 1/4 cup unsalted butter
- 1/3 cup brown sugar
- 8–10 canned pineapple rings, cut into quarters or chunks
- Maraschino cherries (1 per cookie, halved if small)
Instructions
- Preheat oven to 350°F (175°C). Grease your muffin tin thoroughly.
- Make the glaze: In a small saucepan, melt 1/4 cup butter with 1/3 cup brown sugar. Stir until smooth and bubbling. Remove from heat.
- Assemble the topping: Spoon 1 teaspoon of glaze into each muffin cup. Add a pineapple chunk and a cherry.
- Make the cookie dough: Cream butter and sugars until fluffy. Add egg and vanilla; mix until smooth. Stir in flour, baking soda, and salt until a soft dough forms.
- Scoop dough into muffin cups on top of pineapple. Gently flatten the tops.
- Bake 12–14 minutes (mini muffin tin) or 16–18 minutes (standard), until edges are golden and centers set.
- Cool for 5 minutes, then run a knife around the edges and invert cookies onto a wire rack while still warm.
- Cool completely before serving—or enjoy slightly warm for gooey perfection.
Notes
- Drain pineapple well to avoid sogginess.
- Add coconut flakes to the dough for extra tropical flavor.
- Use almond extract for a floral twist.
- Add a splash of rum or pineapple liqueur to the glaze for an adult version.
- Try parchment muffin liners to prevent sticking.
- Prep Time: 20 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Nutrition
- Serving Size: 1 cookie
- Calories: 190
- Sugar: 15g
- Sodium: 105mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 24g
- Fiber: 0g
- Protein: 1g
- Cholesterol: 30mg
Keywords: pineapple upside down cookies, tropical dessert, summer cookie, fruit cookie