Pineapple Upside Down Sugar Cookies are a playful reinterpretation of the classic cake, transforming its caramelized fruit topping into individual handheld treats. Each cookie features a buttery sugar cookie base crowned with sweet pineapple, brown sugar, and a bright maraschino cherry. The result is a tender, golden cookie with a glossy, caramelized fruit top and nostalgic flavor in every bite.

Why You’ll Love This Recipe

• Classic Flavor, Fun Format – All the charm of pineapple upside-down cake in an easy-to-serve cookie.
• Caramelized Fruit Topping – Brown sugar melts into a glossy layer beneath the pineapple rings.
• Buttery Sugar Cookie Base – Soft, tender crumb provides the perfect contrast to juicy fruit.
• Visually Stunning – Pineapple rings and cherries create a bakery-worthy presentation.
• Great for Gatherings – Individually portioned and easy to transport.
• Beginner-Friendly Dough – Simple creaming method with no complicated techniques.

Ingredients You’ll Need

For the Sugar Cookie Dough

• 2 cups all-purpose flour – Provides structure and stability for the cookies.
• 1 cup granulated sugar – Sweetens and contributes to tender texture.
• ½ cup unsalted butter, softened – Adds richness and allows proper creaming.
• 1 large egg – Binds ingredients and adds moisture.
• 1 teaspoon baking powder – Ensures light lift and softness.
• ¼ teaspoon salt – Balances sweetness and enhances flavor.

For the Topping

• 6 canned pineapple rings (cut in halves if needed) – Provide signature sweetness and moisture; pat dry before using.
• ½ cup brown sugar – Melts and caramelizes beneath the pineapple.
• 12 maraschino cherries – Add bright color and classic flavor contrast.

Step-by-Step Instructions

Preheat and Prepare

Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and promote even browning.

Cream Butter and Sugar

In a mixing bowl, beat softened butter and granulated sugar together for 2–3 minutes until light and fluffy; this incorporates air for a tender texture.

Add Egg and Dry Ingredients

Mix in the egg until fully combined. Gradually add flour, baking powder, and salt, mixing just until a soft dough forms without overworking.

Prepare the Pineapple Base

Pat pineapple rings dry with paper towels to remove excess moisture. Place a spoonful of brown sugar in the center of each ring and top with a maraschino cherry.

Assemble the Cookies

Arrange pineapple rings cherry-side down on the prepared baking sheet. Scoop a portion of cookie dough onto the center of each ring, gently pressing to secure.

Bake Until Golden

Bake for approximately 15 minutes, or until the cookie edges turn lightly golden and set. The brown sugar should melt and begin to caramelize.

Cool and Serve

Allow cookies to cool on the baking sheet for 5–10 minutes before carefully transferring to a wire rack. Serve once fully cooled for best structure.

Recipe Notes & Tips

• Drain Pineapple Thoroughly – Excess moisture can cause spreading or soggy bottoms.
• Soften Butter Properly – Butter should be pliable but not melted for ideal creaming.
• Do Not Overmix Dough – Overmixing develops gluten and can toughen cookies.
• Watch the Bake Time – Remove once lightly golden to maintain softness.
• Use Parchment Paper – Prevents sticking from melted brown sugar.
• Cool Before Moving – Caramelized sugar firms as it cools, helping cookies hold shape.

Nutritional Information

• Prep Time: 20 minutes
• Cooking Time: 15 minutes
• Total Time: 35 minutes
• Servings: 12 cookies
• Calories: Approximately 220 kcal per cookie
• Fat: 8g
• Carbohydrates: 35g
• Protein: 2g
• Sugar: 20g
• Fiber: 1g

Perfect Pairings

• Vanilla Ice Cream – Enhances the caramelized pineapple flavor.
• Fresh Whipped Cream – Adds light, creamy contrast.
• Hot Coffee or Espresso – Balances sweetness with bitterness.
• Tropical Fruit Salad – Complements the pineapple notes.

Ideal Occasions

• Summer Parties – Bright tropical flavors fit warm-weather gatherings.
• Holiday Dessert Tables – Eye-catching and festive.
• Bake Sales – Unique twist that stands out among standard cookies.
• Family Baking Days – Fun and approachable for all ages.

Storage & Serving Tips

• Store in Airtight Container – Keep at room temperature for up to 3 days.
• Refrigerate for Longer Storage – Up to 5 days; bring to room temperature before serving.
• Avoid Stacking While Warm – Prevents sticking from caramelized topping.
• Serve Slightly Warm – A brief 5-second microwave refresh enhances softness.

Creative Variations to Try

• Coconut Pineapple Version – Add shredded coconut to the dough for tropical flair.
• Spiced Brown Sugar Twist – Mix a pinch of cinnamon into the brown sugar.
• Mini Cookie Bites – Cut pineapple into smaller pieces for bite-sized treats.
• Rum Glaze Finish – Brush a light rum syrup over warm cookies for depth.

Troubleshooting Common Issues

• Cookies Spreading Too Much – Chill dough for 20 minutes before baking.
• Soggy Centers – Ensure pineapple rings are thoroughly dried.
• Burnt Sugar Bottoms – Reduce bake time slightly and monitor closely.
• Sticky Removal – Use a thin spatula and lift gently once cooled.

Why This Recipe Works

The creaming method incorporates air into the butter and sugar, producing a soft, tender crumb. Baking powder provides light lift without making the cookie cakey. Brown sugar beneath the pineapple melts and caramelizes in the oven, creating a glossy topping similar to traditional upside-down cake. Patting the pineapple dry reduces excess moisture, preventing structural issues while allowing caramelization to occur. At approximately 220 calories per cookie, these treats deliver indulgent sweetness in a controlled, portion-friendly format.

Final Thoughts

Pineapple Upside Down Sugar Cookies offer a charming fusion of nostalgic cake flavors and classic sugar cookie texture. Their caramelized fruit topping, buttery base, and vibrant presentation make them ideal for celebrations or everyday indulgence. For a lighter approach, reduce the brown sugar slightly or use smaller pineapple pieces for mini portions. However you serve them, these cookies promise tropical sweetness and irresistible appeal in every bite.