Imagine everything you love about a pineapple upside-down cake those golden, caramelized pineapple rings, sweet cherries, and buttery brown sugar goodness shrunk down into a soft, chewy sugar cookie. Yep, Pineapple Upside Sugar Cookies are exactly that! These little gems are the perfect combo of tropical flavor and classic cookie charm. Sweet, sticky, fruity, and buttery, they’re eye-catching, totally delicious, and ridiculously easy to make. One bite and you’ll be hooked. Trust me these are sunshine in cookie form.

Why You’ll Love Pineapple Upside Sugar Cookies

This recipe isn’t just about the ingredients it’s about creating moments. Whether you’re cooking for a casual family dinner, hosting a get-together with friends, or simply indulging in some comforting flavors for yourself, this dish is versatile enough to fit the occasion. Here’s why it’s a favorite:
Versatile: Great for birthdays, barbecues, bake sales, or a cozy weekend treat.
Budget-Friendly: Made with simple pantry staples plus a can of pineapple and cherries.
Quick and Easy: No complicated steps just mix, scoop, bake, and flip!
Customizable: Add a little coconut or rum extract for a fun twist.
Crowd-Pleasing: A guaranteed hit with both kids and adults. It’s always a win when a single dish can satisfy everyone at the table. This recipe strikes the perfect balance of flavor and comfort, making it a universal favorite.

Ingredients in Pineapple Upside Sugar Cookies

These cookies are all about bright tropical flavor meeting soft, chewy cookie goodness. Here’s what goes into making them so irresistible:

Sugar Cookie Dough: Use homemade or store-bought either works beautifully as the base.

Crushed Pineapple or Pineapple Tidbits: Drained well so the cookies don’t get soggy.

Maraschino Cherries: Sweet and festive they’re the cherry on top (literally).

Brown Sugar: Gives the “upside-down” base that classic caramelized flavor.

Butter: For that rich, melt-in-your-mouth base and buttery cookie finish.

Vanilla Extract: Adds warmth and sweetness to the dough.

Optional Coconut Flakes: Adds texture and a tropical flair.

Optional Rum Extract: Just a touch brings out the pineapple flavor even more.

(Note: the full ingredients list, including measurements, is provided in the recipe card directly below.)

Instructions

Let’s dive into the steps to create this flavorful masterpiece:

Preheat Your Equipment: Preheat your oven to 350°F and line a muffin tin with parchment or lightly grease each cup.

Combine Ingredients: In a mixing bowl, prepare or scoop your sugar cookie dough. If making from scratch, beat softened butter and sugar until fluffy, then mix in egg and vanilla.

Prepare Your Cooking Vessel: In each muffin cup, place about 1 teaspoon of brown sugar and a small dab of butter. Add one pineapple piece and half a maraschino cherry in the center.

Assemble the Dish: Scoop a ball of sugar cookie dough and press it gently over the pineapple-cherry base in each muffin cup, covering it completely.

Cook to Perfection: Bake for 12–15 minutes, or until the cookies are lightly golden and set.

Finishing Touches: Let cool in the pan for 5–10 minutes. Carefully flip each cookie out onto a cooling rack or tray to reveal the caramelized top.

Serve and Enjoy: These are best served warm, when the pineapple topping is sticky and glossy—but they’re delicious at room temp too!

Nutrition Facts:

Servings: 12
Calories per serving: 210

Preparation Time

Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes

How to Serve Pineapple Upside Sugar Cookies

This dish pairs wonderfully with various sides and accompaniments. Here are a few serving suggestions to enhance your dining experience:
Serve warm with a scoop of vanilla ice cream or whipped cream for a dreamy dessert.
Dust with a pinch of cinnamon or drizzle with caramel sauce.
Pair with a tropical drink like pineapple juice or iced coconut latte.
Add to a summer dessert platter with other fruit-based sweets.

Additional Tips

Here are some extra tips to help you get the most out of this recipe:
Drain pineapple thoroughly to avoid excess moisture.
Use a nonstick muffin tin or parchment to make flipping easy.
Grease muffin cups well to help with releasing the cookies cleanly.
Use crushed pineapple for smaller cookies or tidbits for a chunkier texture.
Don’t overbake cookies should be just set and lightly golden.
Chill the dough for easier handling if it’s sticky.
Add a pinch of salt to balance the sweetness.
These can be made mini-size in a mini muffin pan for bite-sized treats.
Add chopped nuts to the brown sugar base for extra texture.
Store leftovers in an airtight container; reheat briefly to refresh the caramel top.

FAQs

1. Can I use canned pineapple?
Yes just make sure to drain it well to avoid soggy cookies.

2. Do I need to use a muffin tin?
Yes, it helps shape the cookies and hold the toppings in place during baking.

3. Can I use store-bought dough?
Absolutely! It’s a great shortcut and still turns out delicious.

4. What if the cookies stick to the pan?
Let them cool slightly, then run a butter knife around the edges before flipping.

5. Can I make these ahead of time?
Yes, but they’re best the day you make them. Reheat gently to refresh.

6. Can I use fresh pineapple?
You can, but it must be chopped very small and patted dry.

7. Can I freeze them?
Yes wrap tightly and thaw before serving. Reheat slightly to restore texture.

8. How do I prevent soggy bottoms?
Drain pineapple very well and don’t overload the base with butter.

9. Can I make them gluten-free?
Yes, use a 1:1 gluten-free flour blend in your cookie dough.

10. Can I make a big version in a cake pan?
Totally just layer everything in a round pan like a mini upside-down cake and slice like bars.

Conclusion

Pineapple Upside Sugar Cookies are that delightful, chewy, fruity twist on a nostalgic dessert that you didn’t know you needed but now won’t want to live without. Sweet, golden, and loaded with tropical flavor, they’re as charming as they are tasty. Perfect for parties, gifting, or just a midweek pick-me-up, these cookies bring joy in every little bite. So grab your pineapple, preheat that oven, and get ready to flip for these irresistible treats!

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