Pineapple Upside-Down Sugar Cookies

Why You’ll Love This Recipe

Pineapple Upside-Down Sugar Cookies are a fun and delicious twist on a classic dessert. These individual treats feature buttery sugar cookies topped with caramelized pineapple rings and maraschino cherries, baked upside down for a gooey, golden topping. Perfect for parties, picnics, or anytime you want a tropical-flavored treat with nostalgic flair—no need to slice a full cake!

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

1 roll sugar cookie dough (or homemade sugar cookie dough)
1 can pineapple rings (drained and patted dry)
maraschino cherries
1/4 cup brown sugar
3 tablespoons unsalted butter (melted)
cooking spray or muffin tin liners

Directions

1. Preheat the Oven:
   • Preheat oven to 350°F (175°C). Lightly grease a muffin tin or line with paper liners.
2. Prepare the Topping:
   • In a small bowl, mix melted butter and brown sugar. Spoon a small amount (about 1–2 teaspoons) into the bottom of each muffin cup.
   • Place one pineapple ring (cut in half to fit if needed) into each cup. Add one maraschino cherry in the center.
3. Add the Cookie Dough:
   • Roll cookie dough into 1–1.5 inch balls and press gently on top of each pineapple ring. Flatten slightly so they bake evenly.
4. Bake:
   • Bake for 12–15 minutes, or until the cookie tops are golden brown and set.
5. Cool and Flip:
   • Let the cookies cool in the pan for about 5 minutes. Run a knife around the edges if needed, then carefully flip each cookie out onto a wire rack or tray so the pineapple side is on top.
6. Serve:
   • Let cool completely or serve warm for a gooey, cake-like texture.

Servings and Timing

This recipe makes about 12 cookies.
Preparation time: 10 minutes
Baking time: 12–15 minutes
Cooling time: 5–10 minutes
Total time: 30 minutes

Variations

• Add Coconut: Sprinkle shredded coconut in the muffin cups before adding the cookie dough.
• Spice It Up: Add a pinch of cinnamon or nutmeg to the brown sugar mixture for warm flavor.
• Mini Version: Use mini muffin tins and cut the pineapple rings into smaller pieces.

Storage/Reheating

Store in an airtight container at room temperature for up to 3 days.
Reheat briefly in the microwave (about 10 seconds) for a warm, gooey treat.

FAQs

Can I use homemade sugar cookie dough?
Yes! Any sugar cookie dough will work—just make sure it’s not too soft or sticky.

Can I make these ahead of time?
Yes, bake and store them in the fridge. Bring to room temperature or reheat before serving.

Do I have to use muffin tins?
Yes, to help the cookies hold their shape and contain the caramelized topping, muffin tins work best.

Conclusion

Pineapple Upside-Down Sugar Cookies bring the tropical, buttery flavor of the classic cake to an easy-to-serve, handheld treat. Perfect for summer parties or a sweet afternoon snack, these cookies are a playful way to enjoy a nostalgic dessert with a fun twist!

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