Pineapple Upside Sugar Cookies Recipe

Today I’m bringing you a truly inspired twist on two classic desserts: the comforting simplicity of a sugar cookie and the retro charm of Pineapple Upside-Down Cake! If you’re looking for a dessert that’s guaranteed to bring a smile to everyone’s face, trust me, this is the one. These cookies are a total game-changer—a soft, buttery sugar cookie base topped with that warm, caramelized brown sugar, bright pineapple, and a gorgeous little maraschino cherry crown. They bake right in a muffin tin, making them perfectly sized and outrageously cute. Get ready, because these cookies are UNREAL.

Why You’ll Love This Recipe

You know how some recipes just feel like sunshine in a bite? These cookies are exactly that!

• Retro Revival: It takes the nostalgic, gorgeous flavor of a classic pineapple upside-down cake and transforms it into an easy-to-handle, perfectly portioned cookie.
• Buttery Soft Base: The sugar cookie dough is incredibly rich and tender, acting as the perfect counterpoint to the sweet, tangy topping.
• Picture-Perfect: Baking them in a muffin tin ensures every cookie has a beautiful caramelized top (which becomes the bottom, then the top again!), making them look just as incredible as they taste.
• Simple Ingredients, Major Impact: You probably have most of the ingredients on hand, but the final result tastes like you spent hours crafting a gourmet treat.

Ingredients

All you need for this Pineapple Upside Sugar Cookies magic, and less than an hour! Yes, it’s that easy. But first, gather up these goodies:

• Unsalted Butter, softened: The foundation of our dreamy sugar cookie dough, giving it that necessary richness and tenderness.
• Granulated Sugar: Sweetens the dough and helps cream beautifully with the butter for a light, fluffy texture.
• Large Eggs: Binds the ingredients together and adds structure to keep the cookies perfectly intact.
• Vanilla Extract: Crucial for that classic, warm sugar cookie flavor. Don’t skip it!
• All-Purpose Flour: Provides the main structure for our soft, chewable cookie base.
• Baking Powder & Baking Soda: Our leavening duo! They ensure the cookie rises just enough to be tender without becoming a flat disc.
• Salt: Balances the sweetness and enhances all the delicious flavors in the dough.
• Milk: Adds moisture to create a soft, pliable dough that spreads gently over the fruit topping.
• Canned Pineapple Rings, drained: The star of the show! Make sure they are well-drained so they don’t make the topping too soggy. Cut them into small, manageable pieces.
• Maraschino Cherries, halved: Adds that iconic pop of color and a touch of sweet, almond-like flavor to the center of the topping.
• Brown Sugar: Creates the beautiful, deeply caramelized and sticky topping when mixed with melted butter.
• Melted Butter (for the topping): Combines with the brown sugar to form the signature gooey, fragrant layer at the base of the cookie.

Note: The precise measurements for all of these ingredients, along with the full, printable recipe, will be found right under this article in the recipe card!

How to Make the Pineapple Upside Sugar Cookies

Step 1: Prep the Pan and the Topping

Preheat your oven to 350∘F (175∘C). Now, grab a muffin tin and spray those cups generously! In a small bowl, whisk together the melted butter and brown sugar. Place about 1 teaspoon of this dreamy mixture into the bottom of each muffin cup. Top that with a small piece of pineapple and half of a cherry right in the center.

Step 2: Cream the Dough

In a large mixing bowl (or using a stand mixer!), cream together your softened butter and granulated sugar until they are light, fluffy, and look nearly white. This step is key to a tender cookie! Beat in the eggs one at a time, then mix in the vanilla extract.

Step 3: Combine Dry Ingredients

In a separate medium bowl, whisk together the flour, baking powder, baking soda, and salt. Give it a good mix to make sure the leavening is evenly distributed.

Step 4: Mix the Dough

Gradually add your dry ingredients into the wet mixture, alternating with the milk, until a soft, wonderful cookie dough forms. Be careful not to overmix it!

Step 5: Scoop and Bake

Scoop about 2 tablespoons of dough into each muffin cup. Gently spread the dough with the back of a spoon to cover the fruit and brown sugar layer completely. Bake for 15-18 minutes, or until the edges are lightly golden.

Step 6: The Reveal!

This is the exciting part! Let the cookies cool for about 5 minutes right in the muffin tin. Then, place a wire cooling rack or a piece of parchment paper over the tin and carefully (but swiftly!) invert the whole thing. The cookies should pop out, revealing that beautiful, caramelized pineapple and cherry on top! Let them cool completely before diving in.

Pro Tips for Making the Recipe

• Room Temperature is Key: Make sure your butter and eggs are truly at room temperature. This allows them to emulsify (blend) properly, resulting in a much lighter and fluffier cookie dough.
• Drain the Pineapple Like a Pro: Pineapple rings come packed in juice. Drain them very well—I even like to blot the pieces on a paper towel before placing them in the tin. Less moisture means a better-caramelized topping!
• Don’t Overfill the Cups: Stick to about 2 tablespoons of dough per cup. Overfilling can cause them to dome too much and make them hard to invert.
• Grease Generously: Even if you’re using a non-stick tin, spraying with non-stick cooking spray is a must. It guarantees that satisfying, clean release when you invert the cookies.

How to Serve

These cookies are gorgeous and complete all on their own, but if you want to elevate the dessert experience, here are a few fun ideas:

• A La Mode: Serve them still slightly warm with a small scoop of vanilla ice cream on the side—it’s like a mini cake sundae!
• A Drizzle of Glaze: If you like an extra touch of sweetness, drizzle a simple powdered sugar glaze (powdered sugar + a tiny bit of pineapple juice) over the cooled cookies.
• Morning Treat: Honestly, they’re fantastic paired with a hot cup of coffee for a slightly sweet breakfast or brunch treat.
• Tropical Flair: Pair them with a scoop of coconut sorbet or a sprinkle of toasted coconut flakes.

Make Ahead and Storage

Storing Leftovers

Place cooled cookies in an airtight container at room temperature for up to 3 days. I recommend placing a piece of parchment paper between layers to prevent the sticky topping from making a mess.

Freezing

You can freeze the baked cookies! Once completely cool, place them in a single layer on a baking sheet to flash freeze for an hour. Then, transfer them to a freezer-safe zip-top bag or container for up to 3 months.

Reheating

There’s no need to reheat them, as they are delicious at room temperature. However, if you want that “just-baked” warmth, pop them in a 300∘F (150∘C) oven for about 5 minutes.

FAQs

1. Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works beautifully, but you must make sure to cut it into very small pieces and remove the tough core. Just like with canned, ensure the pieces are blotted dry before placing them into the muffin tin to minimize excess liquid that could prevent the topping from caramelizing properly.

2. Why did my cookies stick to the muffin tin when I inverted them?

This is usually a result of not applying enough fat to the pan or trying to flip them too soon or too late. Make sure to grease your muffin tin generously, even if it’s non-stick. Also, flipping them after the 5-minute cool-down period is critical. If they cool too long, the caramelized sugar can harden and glue them to the pan.

3. Can I make this cookie dough ahead of time?

Yes, you can! You can prepare the dough and keep it tightly wrapped in the refrigerator for up to 3 days. Before scooping, let it sit out for about 15-20 minutes to soften slightly, making it easier to spread gently over the fruit topping in the muffin cups.

4. What’s the best way to get them to pop out cleanly when I invert them?

The trick is confidence! After the 5-minute cool-down, place a baking sheet or a cooling rack firmly over the muffin tin. Using oven mitts, hold the tin and the sheet/rack tightly together and flip the whole stack over with a swift, confident motion. If a cookie is stubborn, you can use a small, offset spatula to gently coax it out.