Name: Pineapple Upside Down Sugar Cookies Recipe
Prep time: 20 min
Cook time: 22 min
Total time: 42 min
Cuisine: American
Ingredients: 1 cup butter, room temperature; 1 ½ cups granulated sugar; 2 eggs; 2 tsp vanilla extract; ½ cup sour cream; 3 cups all-purpose flour; 1 tsp baking powder; 1 tsp cornstarch; ½ tsp salt; 13 canned pineapple slices; 13 maraschino cherries; ½ cup butter, melted; 1 cup light brown sugar, packed

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If you’re craving a cookie that’s bursting with tropical charm and a delightful twist, you absolutely have to try this Pineapple Upside Down Sugar Cookies Recipe. These cookies take the classic sweetness of sugar cookies and elevate them with the rich, caramelized goodness of brown sugar, buttery pineapple slices, and bright maraschino cherries. They’re perfect for when you want to surprise your friends or family with something both nostalgic and refreshingly different. Every bite offers a chewy, buttery base paired with that unmistakable pineapple upside down cake vibe turned cookie—trust me, it’s a total crowd-pleaser!

Pineapple Upside Down Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

You don’t need an overwhelming list of ingredients to make this cookie magic happen—just a handful of kitchen staples that come together beautifully. Each component plays a crucial role from the rich butter that ensures tender crumb to the pineapple and cherries that bring vibrant color and juicy sweetness.

Butter (1 cup, room temperature): This adds richness and creates that soft, melt-in-your-mouth texture you want in a sugar cookie.
Granulated sugar (1 ½ cups): The classic sweetener that balances the flavors and helps with browning.
Eggs (2): They bind the dough and contribute to a tender crumb.
Vanilla extract (2 tsp): It elevates the flavor with a warm, floral sweetness.
Sour cream (½ cup): Adds moisture and slight tang for a perfect cookie softness.
All-purpose flour (3 cups): The foundation that gives structure to your cookies.
Baking powder (1 tsp): Provides just the right lift to keep them light.
Cornstarch (1 tsp): Helps create a delicate, tender texture.
Salt (½ tsp): Enhances all the sweet flavors without overpowering.
Pineapple slices (13 canned): These give the cookies their signature tropical topping and a juicy burst.
Maraschino cherries (13): Bright, sweet, and visually stunning at the cookie’s center.
Butter, melted (½ cup): Combines with brown sugar to make that luscious caramel base.
Light brown sugar, packed (1 cup): Adds rich, molasses-note sweetness that caramelizes perfectly under the pineapple.

How to Make Pineapple Upside Down Sugar Cookies Recipe

Step 1: Prepare the Caramelized Cookie Base

The magic of the Pineapple Upside Down Sugar Cookies Recipe starts with a buttery, caramelized brown sugar layer. Begin by combining the melted butter and light brown sugar. Spoon about one tablespoon of this mixture into the bottom of each cavity of your prepared cookie pan. Spread evenly to form a sticky, sweet base that will caramelize beautifully beneath the fruit.

Step 2: Arrange the Pineapple and Cherry Toppings

Next, gently place one pineapple slice into each cavity over the brown sugar layer. Center a maraschino cherry right in the middle of each pineapple slice to add that signature pop of color and a burst of sweetness. This step is key because not only does it look gorgeous, but as the cookie bakes, the juices mingle and infuse into the surrounding dough.

Step 3: Mix the Cookie Dough

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in eggs one at a time, followed by the vanilla extract for that rich aroma we all love. Stir in the sour cream to keep the cookies tender and moist. In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt; then gradually add this dry mix to your wet ingredients until just combined. Resist overmixing to keep the dough perfectly tender.

Step 4: Fill the Cookie Pan and Bake

Divide the cookie dough evenly and gently spoon it over the pineapple and cherry layer in each cavity, smoothing lightly. This is where patience pays off because you want an even layer of dough so your cookies bake perfectly around the sweet fruit topping. Bake in a preheated oven (usually 350°F) for about 18-20 minutes, or until the edges are golden and a toothpick inserted near the cookie’s edge comes out clean.

Step 5: Cool and Release

Let the pan cool for about 10 minutes; then carefully run a knife around each cookie to loosen. Invert the pan onto a cooling rack so the caramelized pineapple and cherry topping shine on top. This is the moment you see the signature upside down transformation—a gorgeous, glossy, and fruity cookie that’s ready to be devoured!

How to Serve Pineapple Upside Down Sugar Cookies Recipe

Garnishes

While these cookies are stunning as they come, adding a light dusting of powdered sugar or a drizzle of honey just before serving can elevate their appeal. Fresh mint leaves beside the plate add a pop of green color and a refreshing hint that complements the sweetness.

Side Dishes

These cookies pair wonderfully with a cool cup of tea, a fresh tropical smoothie, or a scoop of vanilla ice cream. You could also serve alongside a fresh fruit salad to emphasize their fruity, summery vibe — perfect for brunch or an outdoor gathering.

Creative Ways to Present

Try arranging the Pineapple Upside Down Sugar Cookies Recipe on a wooden board or colorful platter surrounded by pineapple chunks and cherries for a festive display. For parties, layer them in a glass jar with parchment paper between layers for a charming gift idea or ‘grab-and-go’ treat box.

Make Ahead and Storage

Storing Leftovers

These cookies keep wonderfully in an airtight container at room temperature for up to 4 days. The flakes stay soft, and that irresistible pineapple topping remains juicy and flavorful. If you want to refresh them a bit, just a short warm-up (see below) works wonders.

Freezing

If you want to save some for later, freeze the cookies in a single layer on a baking sheet until firm, then transfer to a zip-top freezer bag or airtight container. They freeze well for up to 3 months. When you’re ready for a treat, just thaw them overnight in the fridge.

Reheating

To revive the fresh-baked feel, warm your cookies in a 300°F oven for about 5 minutes. This softens the dough and re-melts some of the caramelized topping to bring back that gooey brightness that makes these cookies truly special.

FAQs

Can I use fresh pineapple instead of canned?

Fresh pineapple can work but it has more moisture than canned, so it may affect the cookie consistency and caramelization. If you do use fresh, be sure to pat the slices dry and watch the baking time closely.

Do I have to use maraschino cherries?

Maraschino cherries add iconic color and sweetness, but you can swap them for glacé cherries or even small berries if you prefer. Just choose something that complements the pineapple and withstands baking.

Can I make this recipe gluten-free?

Yes! Use a one-to-one gluten-free flour blend that includes xanthan gum. Texture might be slightly different but the overall flavor will be just as delicious.

Is sour cream necessary in the dough?

Sour cream adds moisture and a slight tang that balances sweetness beautifully. If you don’t have it, plain Greek yogurt can be a good substitute.

How do I prevent the cookies from sticking to the pan?

Make sure to thoroughly grease your pan or use silicone liners for easier release. Also, allowing the cookies to cool before flipping helps keep their shape intact.

Final Thoughts

This Pineapple Upside Down Sugar Cookies Recipe combines the best of two worlds—classic sugar cookies and the nostalgic charm of pineapple upside down cake in one irresistibly delicious bite. Whether you’re baking for a family gathering, holiday party, or just a fun weekend treat, I promise these cookies will leave smiles all around. Give them a try and watch how quickly they disappear!