Pineapple Upside-Down Cookies
These Pineapple Upside-Down Cookies transform the beloved classic cake into a portable, handheld treat packed with all the nostalgic flavors you love. Each cookie features a buttery caramelized brown sugar base, sweet crushed pineapple, and a maraschino cherry center — baked right in a muffin tin and flipped out for a stunning presentation. Soft and chewy with slightly crisp edges, they're easier than the original cake, make-ahead friendly, and always the first thing to disappear at any gathering.
Equipment
- Standard 12-cup muffin tin Two tins needed for a full batch of 24 cookies
- Mixing bowls One medium, one large
- Electric mixer or stand mixer For creaming butter and sugars
- Measuring cups and spoons
- Cookie scoop (optional) Helps portion dough evenly
- Wire cooling rack
- Parchment paper or non-stick spray
- Small bowl For draining pineapple
- Paper towels For patting cherries dry
- Fine-mesh strainer (optional) For pressing excess liquid from pineapple
- Large cutting board or baking sheet For flipping the muffin tin
- Butter knife For loosening cookies from pan edges
Ingredients
For the Topping
- 6 tablespoons unsalted butter 85g, melted
- ¾ cup light brown sugar 165g, packed
- 20 oz crushed pineapple 1 can (565g), drained very well
- 24 maraschino cherries drained and patted dry
For the Cookie Dough
- ½ cup unsalted butter 113g (1 stick), softened to room temperature
- ½ cup granulated sugar 100g
- ½ cup light brown sugar 110g, packed
- 1 large egg room temperature
- 1 teaspoon vanilla extract 5ml; pure vanilla recommended
- 1¾ cups all-purpose flour 218g
- ½ teaspoon baking soda
- ½ teaspoon salt
- ¼ teaspoon ground cinnamon
Instructions
- Preheat your oven to 350°F (175°C) and generously spray a standard 12-cup muffin tin with non-stick cooking spray, coating the sides and bottom of each cup. Set aside; repeat with a second tin if making the full batch.
- Stir together the melted butter and brown sugar in a small bowl until smooth, then spoon about 1 tablespoon of the mixture into the bottom of each muffin cup, spreading it evenly with the back of the spoon.
- Spoon about 1 tablespoon of well-drained crushed pineapple over the brown sugar layer in each cup and press lightly to flatten, then place one dry maraschino cherry in the center of each, pressing gently so it sits secure.
- Beat the softened butter with an electric mixer on medium speed for 1 minute until creamy, then add both sugars and beat on medium-high for 2–3 minutes until light, fluffy, and increased in volume.
- Add the egg and vanilla extract to the butter-sugar mixture and beat until fully incorporated, scraping down the bowl as needed — a slightly curdled appearance at this stage is normal.
- In a separate medium bowl, whisk together the flour, baking soda, salt, and cinnamon until evenly combined and lump-free.
- Add the dry ingredients to the wet ingredients all at once and mix on low speed just until no dry streaks remain — stop as soon as the dough comes together to keep cookies tender.
- Scoop about 2 tablespoons of dough per cookie and place on top of the pineapple-cherry layer in each muffin cup, pressing gently to spread the dough to almost the edges of each cup.
- Bake on the center rack for 12–14 minutes, until the tops are lightly golden and spring back when touched — edges should look set while centers may appear slightly soft.
- Let cookies cool in the pan for exactly 5 minutes, then run a butter knife around each edge, place a large cutting board over the tin, and carefully flip the entire tin upside down to release the cookies topping-side up. Cool completely on a wire rack before serving.
Notes
- Drain pineapple thoroughly: Press crushed pineapple in a fine-mesh strainer or squeeze in paper towels until very little liquid remains — excess moisture causes soggy cookies.
- Don't skip the 5-minute rest: This is the magic window when caramel is set enough to hold but still soft enough to release cleanly from the pan.
- Use room temperature butter: Softened butter creams better with sugar, yielding a lighter, chewier cookie texture.
- Be generous with non-stick spray: Coat the sides of each muffin cup thoroughly, as the caramel can bond strongly to uncoated surfaces.
- Pat cherries completely dry: Excess cherry moisture makes the topping runny — a few passes with a paper towel makes a big difference.
- Work quickly when flipping: The longer cookies sit in the pan after baking, the more likely the hardened caramel will stick — don't wait past the 5-minute mark.
- Coconut variation: Add ½ cup shredded coconut to the dough and sprinkle toasted coconut on top after baking for a tropical twist.
- Fresh pineapple substitute: Finely chop fresh pineapple and simmer for 10 minutes to evaporate excess liquid before cooling and using — canned is recommended for convenience.
- Storage: Store in an airtight container at room temperature for up to 3 days, refrigerated for up to 1 week, or frozen for up to 3 months.
- Reheat tip: Microwave individual cookies for 10–15 seconds to soften the caramel and restore that fresh-baked texture.
Nutrition
Serving: 1CookieCalories: 165kcalCarbohydrates: 25gProtein: 1.5gFat: 7gSaturated Fat: 4gPolyunsaturated Fat: 0.4gMonounsaturated Fat: 2gCholesterol: 25mgSodium: 95mgPotassium: 55mgFiber: 0.5gSugar: 17gVitamin A: 4IUVitamin C: 3mgCalcium: 2mgIron: 4mg
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