Pineapple Upside Sugar Cookies

These Pineapple Upside Sugar Cookies are what happens when classic pineapple upside-down cake meets soft, chewy sugar cookies—and it is glorious. Buttery sugar cookie bases are topped with caramelized pineapple, a maraschino cherry, and a glossy brown sugar glaze that’s baked right in. They’re bite-sized tropical sunshine with retro flair and modern convenience.

Before we jump in, I just want to say a heartfelt thank you for stopping by. Whether you’re here for nostalgic sweets or looking for something unique to share at your next gathering, I’m so glad you’re here. Want recipes like this sent straight to your inbox? Subscribe below and let’s bake more joyful bites together!

What Are Pineapple Upside Sugar Cookies?

These cookies are inspired by the iconic pineapple upside-down cake—but in cookie form! We take a soft sugar cookie dough, press it into muffin tins or shape it by hand, and top each with a slice of pineapple, a cherry, and a drizzle of brown sugar-butter glaze. As they bake, the pineapple caramelizes slightly and sinks into the dough, creating a gooey, golden, tropical-tasting cookie that’s anything but ordinary.

They’re fun, colorful, and absolutely irresistible.

Why You’ll Love These Cookies

• All the flavor of pineapple upside-down cake with the ease of a cookie
• No fork required—portable and party-ready
• Uses simple, familiar ingredients
• Kid-friendly and freezer-friendly
• That caramelized pineapple topping? Just wait ‘til you try it

What Do They Taste Like?

They’re soft, buttery sugar cookies with gooey, caramelized pineapple and cherry nestled on top. The edges are lightly crisped, while the center stays tender and moist. The pineapple brings brightness and acidity, the brown sugar glaze adds warmth, and the cherry? A sweet little bonus. They taste like summer and comfort all in one bite.

Benefits of This Recipe

• No stand mixer needed—just a bowl and spoon
• Great way to use canned pineapple and pantry staples
• Easy to make ahead
• Show-stopping look with minimal effort
• Adaptable for mini or regular muffin tins

Ingredients for Pineapple Upside Sugar Cookies

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)

Note: You can use pineapple tidbits instead of rings—just make sure they’re well-drained.

Tools You’ll Need

• Muffin tin (mini or standard)
• Mixing bowls
• Hand mixer or wooden spoon
• Saucepan (for glaze)
• Cookie scoop or tablespoon
• Cooling rack

Ingredient Additions & Substitutions

• Add coconut flakes to the dough for a tropical twist
• Use almond extract instead of vanilla for a slightly floral flavor
• Gluten-free flour blend works well in place of all-purpose
• Add a pinch of cinnamon to the glaze for warmth
• Want it boozy? Add a splash of rum or pineapple liqueur to the glaze!

How to Make Pineapple Upside Sugar Cookies

1. Preheat oven to 350°F (175°C). Grease your muffin tin well (don’t skip this step!).
2. Make the glaze: In a small saucepan, melt 1/4 cup butter with 1/3 cup brown sugar over medium heat. Stir until smooth and bubbling. Remove from heat.
3. Assemble the pineapple topping: Spoon about 1 teaspoon of glaze into each muffin cup. Place a pineapple chunk or quarter on top, followed by a cherry.
4. Make the cookie dough:
   • Cream the butter and sugars until fluffy.
   • Add the egg and vanilla, mix until combined.
   • Stir in flour, baking soda, and salt until a soft dough forms.
5. Scoop dough into each muffin cup on top of the pineapple. Use your fingers or a spoon to gently flatten it a bit.
6. Bake for 12–14 minutes (mini muffin tin) or 16–18 minutes (standard muffin tin), until the edges are lightly golden and the centers are set.
7. Cool for 5 minutes, then carefully run a knife around the edges and invert onto a wire rack while still warm so the glaze doesn’t harden in the pan.
8. Cool completely before storing or serving (but they’re incredible slightly warm, too!).

Pro Tip: If your cookies stick a little, place the muffin tin over low heat for 30 seconds—it will help loosen the glaze and release the cookies.

What to Serve With These Cookies

These cookies pair beautifully with:

• A scoop of vanilla or coconut ice cream
• Fresh fruit salad
• Whipped cream and lime zest
• Sparkling water, rosé, or pineapple cocktails
• A sweet brunch board with muffins, scones, and fresh berries

Tips for Success

• Drain pineapple well to avoid soggy cookies
• Don’t overbake—they’ll continue setting as they cool
• Use softened butter, not melted, for best dough texture
• A nonstick muffin tin or parchment liners can help if you’re worried about sticking
• Make a double batch—these disappear fast!

Storage Instructions

• Room Temp: Store in an airtight container for up to 3 days
• Fridge: Store for up to 5 days—just let them come to room temp before serving
• Freezer: Freeze in a single layer, then transfer to a bag for up to 2 months. Thaw and warm slightly for best results

Frequently Asked Questions

Can I use fresh pineapple?

Yes, but make sure it’s cut small and cooked slightly to soften. Canned pineapple is easier and more consistent.

Do I have to use a muffin tin?

A muffin tin gives you that upside-down effect and holds the topping in place. You can bake these flat on a tray, but the topping may spread.

Can I make them ahead?

Yes! Bake and store at room temp for up to 2 days, or freeze and thaw before serving.

Can I make them vegan?

Yes—use plant-based butter and a flax egg. The cookies will be slightly softer but still delicious.

Conclusion

If you’re looking for a treat that’s just as fun to look at as it is to eat, these Pineapple Upside Sugar Cookies are the answer. They’re fruity, gooey, buttery, and filled with tropical flavor. Whether you’re baking for a summer gathering or just need a little sunshine in cookie form, these will win hearts—guaranteed.

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