Pineapple Upside-Down Sugar Cookies Recipe

If you’re looking to add a playful twist to a nostalgic favorite, these Pineapple Upside-Down Sugar Cookies will bring tropical sunshine to your kitchen! Each cookie is the perfect marriage of buttery sugar cookie and the irresistible caramelized pineapple topping, studded with a bright maraschino cherry. Imagine the sweet aromas of brown sugar and pineapple floating through your home, all tucked into adorable, individually portioned treats. These cookies deliver all the show-stopping flavor of the classic cake, but in a form that’s both easy to share and impossible to resist.

Ingredients You’ll Need

This recipe keeps things wonderfully simple yet vibrant, relying on staple pantry items that let the pineapple’s bold sweetness and the cookies’ tender crumb shine through. Each ingredient plays a vital role in building those gorgeous flavors, chewy textures, and lovely colors.

• 1/2 cup unsalted butter, melted (for topping): Gives the topping its rich, luscious base for ultimate caramelization.
• 1/2 cup brown sugar, packed: Adds deep, molasses-y sweetness that pairs perfectly with pineapple.
• 1 can (20 oz) pineapple slices, drained and cut into small pieces: Delivers juicy bites and that signature upside-down flair.
• Maraschino cherries, halved: A cheerful pop of color and classic sweetness in every cookie.
• 1 cup unsalted butter, softened (for cookies): Ensures tender, melt-in-your-mouth sugar cookies.
• 1 cup granulated sugar: Adds classic cookie sweetness and helps create a tender crumb.
• 1 large egg: Binds everything together and adds a rich texture.
• 1 tsp vanilla extract: Infuses warm, fragrant flavor throughout the dough.
• 2 1/2 cups all-purpose flour: Forms a sturdy yet soft cookie base for all that juicy fruit.
• 1 tsp baking powder: Lifts the cookies for just the right amount of fluff.
• 1/4 tsp salt: Sharpens and balances the sweet flavors so nothing tastes flat.

How to Make Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Topping

Preheat your oven to 350°F (175°C) and lightly grease or line a muffin tin with parchment rounds. In a small bowl, combine the melted butter and brown sugar. Spoon about a tablespoon of this luscious mixture into the bottom of each muffin cup—think of it as your foundation for all the tropical goodness to come!

Step 2: Add the Fruit

Now, top that buttery brown sugar with a few pieces of pineapple, arranging them so each cup gets a good ratio of fruit. Grab your halved maraschino cherries and press one gently into the center of the pineapple in each muffin well; that ruby red glow is what gives Pineapple Upside-Down Sugar Cookies their signature look.

Step 3: Mix the Sugar Cookie Dough

In a large bowl, cream your softened butter and granulated sugar together until delightfully light and fluffy. This step is key for tender cookies! Beat in the egg and vanilla extract, mixing until well combined. In a separate bowl, whisk together the flour, baking powder, and salt, then gradually add the dry ingredients to the wet ingredients, mixing until a soft, cohesive dough forms.

Step 4: Assemble the Cookies

Take about 1 1/2 tablespoons of the sugar cookie dough and gently press it over each fruity muffin tin compartment. Use your fingers (or lightly floured hands) to flatten the dough so it covers the pineapple and cherry evenly, sealing in that juicy, caramelized flavor underneath.

Step 5: Bake

Slide the muffin tin into your preheated oven and bake the cookies for 12 to 15 minutes, or until the edges are lightly golden. Let the cookies cool in the tin for 5 minutes so the topping sets up just a bit, then carefully invert the muffin tin over a parchment-lined surface or cooling rack. A little gentle tap may help release them—and then, marvel at your mini masterpieces!

How to Serve Pineapple Upside-Down Sugar Cookies

Garnishes

For a finishing touch, dust your Pineapple Upside-Down Sugar Cookies with a little powdered sugar, or drizzle with a simple vanilla glaze for an extra hint of sweetness. A small dollop of whipped cream or a sprinkle of toasted coconut flakes can take them stratospheric.

Side Dishes

These cookies are lovely with a cup of freshly brewed coffee or a tall glass of milk. If you’re hosting a party, pair them with a fruit salad or a scoop of vanilla ice cream to echo the tropical notes of these Pineapple Upside-Down Sugar Cookies.

Creative Ways to Present

Try stacking a few cookies on a bright cake stand for a festive touch, or nestle them in colorful cupcake liners for parties and potlucks. For special occasions, wrap each Pineapple Upside-Down Sugar Cookie in cellophane with a ribbon—perfect little edible gifts that absolutely wow!

Make Ahead and Storage

Storing Leftovers

To keep your Pineapple Upside-Down Sugar Cookies soft and fresh, store them in an airtight container at room temperature for up to three days. If they start to dry out, a small slice of bread in the container can help keep their texture just right.

Freezing

These cookies freeze remarkably well! Cool them completely, then layer them in a freezer-safe container with parchment between layers to prevent sticking. They’ll keep beautifully in the freezer for up to 2 months—just thaw at room temperature before serving.

Reheating

If you want to recapture that just-baked warmth, pop a Pineapple Upside-Down Sugar Cookie in the microwave for 10–15 seconds, or warm briefly in a low oven. The topping will become glossy and aromatic again, bringing back all those fresh-from-the-oven vibes.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple brings even more brightness to these cookies. Just be sure to cut it into small pieces and pat it dry to remove excess juice, which can otherwise make the topping too runny.

What can I substitute for maraschino cherries?

If cherries aren’t your thing, try using dried cranberries, blueberries, or even small pieces of candied ginger for a fun flavor twist that still pops.

Do I need to line the muffin tin?

While you can simply grease the tin, lining with parchment rounds guarantees even easier release—especially if you want picture-perfect Pineapple Upside-Down Sugar Cookies.

Can I make these gluten-free?

Yes! Substitute a cup-for-cup gluten-free flour blend for the all-purpose flour. Just make sure it includes xanthan gum, or add a pinch yourself, to help the cookies hold together.

Can I make the dough ahead of time?

You sure can. Prepare the sugar cookie dough and refrigerate it (covered) for up to 48 hours. Let it come back to room temperature so it’s easy to press over the fruit layer when you’re ready to assemble and bake.

Final Thoughts

If you’re ready to add a sunny twist to your cookie repertoire, these Pineapple Upside-Down Sugar Cookies are a must. There’s so much joy in both making and sharing them, and every bite is a sweet little vacation. Go ahead—give this recipe a try and delight your friends and family!

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