Irresistible Pineapple Upside Sugar Cookies (Easy Recipe + 10 Tips)

If you’re anything like me, you grew up loving Pineapple Upside-Down Cake at family gatherings—sweet, sticky, and always crowned with that bright red cherry. But what if I told you that you could capture all that retro magic in a cookie? That’s where Pineapple Upside Sugar Cookies come in, and let me tell you, they’re just as charming as they sound.

These cookies are a playful mashup of classic sugar cookies and the tropical flair of pineapple and cherries. They’re buttery, slightly caramelized on top, and bring a bite-sized ray of sunshine to your dessert plate. Plus, they’re a fun way to sneak some fruit into a treat without hearing a single complaint—especially from the littles.

Let’s dive into the deliciousness of these tropical treats. Whether you’re making them for a bake sale, a backyard BBQ, or just because it’s Thursday, these cookies won’t last long!

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Why You’ll Love This Pineapple Upside Sugar Cookies

• Tropical Flavors: The combination of pineapple and maraschino cherries channels instant vacation vibes.
• Soft & Buttery: The base sugar cookie is tender and rich without being overly sweet.
• Crowd-Pleaser: Perfect for potlucks, picnics, or brunch spreads.
• Kid-Approved: Little hands love placing the cherry on top.
• Customizable: Add more pineapple, skip the cherry, or double up on brown sugar for extra caramelization.

Inspired by the classic Pineapple Upside-Down Cake on Allrecipes, these cookies are a delightful shortcut to tropical nostalgia.

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Ingredients

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg
• 1 tsp vanilla extract
• 2 1/2 cups all-purpose flour
• 1/2 tsp baking powder
• 1/4 tsp salt
• 1/2 cup crushed pineapple, well-drained
• 1/4 cup brown sugar
• Maraschino cherries, halved
• Pineapple slices or tidbits (optional for topping)

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Instructions

1. Cream the Butter & Sugar: In a large bowl, beat the softened butter and granulated sugar until light and fluffy (2-3 minutes).
2. Add the Egg & Vanilla: Mix in the egg and vanilla extract until combined.
3. Combine Dry Ingredients: In another bowl, whisk together flour, baking powder, and salt. Slowly incorporate into the wet mixture, mixing on low speed.
4. Fold in Pineapple: Gently fold in the well-drained crushed pineapple. Pat dry with paper towels to prevent soggy dough.
5. Chill: Cover and refrigerate the dough for at least 1 hour.
6. Prepare Toppings: Set out brown sugar in a small bowl for dipping.
7. Shape the Cookies: Preheat oven to 350°F. Scoop 1.5 tablespoons of dough, roll into balls, and slightly flatten.
8. Assemble: Press the top of each dough disc into brown sugar. Optionally top with pineapple tidbits and a cherry half.
9. Bake: Place sugar-side up on a parchment-lined baking sheet. Bake for 10-12 minutes until edges are golden.
10. Cool & Enjoy: Cool on the sheet for 5 minutes before transferring to a wire rack.

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Melania’s Tips for Perfect Pineapple Upside Sugar Cookies

• Drain Pineapple Well: Extra moisture is the cookie’s worst enemy here. Pat, squeeze, and blot like you’re prepping it for a photoshoot.
• Double Brown Sugar Dip: For an ultra-caramelized effect, dip cookies in brown sugar twice.
• Broil Briefly: A quick broil (1-2 minutes) post-bake adds a golden, candied finish—just stay close to that oven!
• Vanilla Boost: Add a splash of pineapple juice with the vanilla for extra zing.

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Bake It With the Littles

Baking with kids? Turn this into a fun assembly line:

• Let them roll dough balls and flatten them.
• Have them dip cookies in brown sugar (expect a little mess—embrace it!).
• Let them crown each cookie with pineapple and a cherry.

Pro tip: Keep extra cherries on hand—some are guaranteed to “disappear.”

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Meal-Prep Magic

These cookies are perfect for prepping ahead:

• Dough Storage: Refrigerate the dough up to 3 days.
• Freezing: Freeze rolled cookie dough balls (without sugar or toppings) for up to 3 months. Just thaw slightly, sugar them up, and bake.
• Baked Cookies: Store in an airtight container at room temp for 4-5 days.

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Healthier Swaps Without Losing the Magic

Want to lighten things up? Try these swaps:

• Whole Wheat Flour: Swap in half whole wheat flour for a nuttier flavor.
• Coconut Sugar: Replace brown sugar with coconut sugar for a lower glycemic option.
• Unsweetened Pineapple: Use pineapple in juice, not syrup, for less added sugar.
• Butter Alternatives: Sub half the butter with unsweetened applesauce—still tender, slightly healthier.

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Leftover Remix

Leftovers? I doubt it, but just in case:

• Ice Cream Sandwiches: Pop a scoop of vanilla bean ice cream between two cookies.
• Trifle Layers: Crumble cookies into a pineapple or tropical trifle.
• Yogurt Parfait: Crumbled cookie bits with Greek yogurt and extra fruit? Yes, please.

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Gift It Like a Pro

These cookies package beautifully:

• Stack them in clear cellophane bags with a ribbon.
• Add a little tag: “A Slice of Sunshine in Every Bite!”
• Pair with a tropical tea blend or pineapple-themed kitchen towel for a charming gift basket.

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FAQs

Can I use fresh pineapple?
Yes, but make sure to finely chop and drain thoroughly to avoid sogginess.

Can I skip the cherry?
Absolutely. The cookie is delightful with just pineapple and brown sugar.

Can I make them gluten-free?
Use a 1:1 gluten-free baking flour. Texture may vary slightly, but they’ll still be delicious.

Why did my cookies spread too much?
The dough was likely too warm or the pineapple wasn’t well-drained. Chill the dough longer next time.

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Final Thought

Pineapple Upside Sugar Cookies are like little bites of joy wrapped in nostalgia and a splash of tropical fun. Whether you’re reviving a vintage classic or creating new family traditions, these cookies bring sunshine to any table. And hey, if you need more retro-inspired treats, check out my Cherry Almond Shortbread Cookies—they’re another crowd-pleaser with a pop of color.

Now, go bake some sunshine! 🌞🍍

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