Pineapple Upside-Down Cookies Recipe

If you love the classic charm of pineapple upside-down cake but want a portable, snackable treat, then these Pineapple Upside-Down Cookies are exactly what your kitchen is craving. Imagine soft, buttery cookies with a luscious caramelized brown sugar base topped with juicy pineapple pieces and bright maraschino cherries, all beautifully revealed when flipped over after baking. They are sweet, tropical, and utterly delightful – perfect for impressing friends, brightening an afternoon coffee break, or just savoring a bite of sunny happiness anytime you want.

Ingredients You’ll Need

Each ingredient in this recipe plays a crucial role in delivering the perfect balance of texture and flavor, making these cookies irresistible. From the tender cookie dough to the sticky, caramelized pineapple topping, every element is simple yet essential.

• Unsalted Butter (½ cup, softened): This gives the cookies a rich, melt-in-your-mouth texture and depth of flavor.
• Granulated Sugar (¾ cup): Adds sweetness and helps create a tender crumb; using brown sugar instead offers a lovely caramel hint.
• Large Egg (1): Binds everything together and keeps the dough moist and chewy; you can swap it with a flax egg if needed.
• Vanilla Extract (1 tsp): Brings warmth and richness, elevating the cookie’s subtle sweetness.
• All-Purpose Flour (1 ¼ cups): The base that gives structure to your cookies, but feel free to go gluten-free with a 1:1 blend.
• Baking Powder (½ tsp): Just enough lift to keep the cookies soft and slightly puffy.
• Salt (¼ tsp): A small but mighty ingredient that balances sweetness and amplifies all the flavors.
• Brown Sugar (½ cup): Creates the signature caramel topping that’s oh-so-irresistible when baked.
• Melted Butter (2 tbsp): Helps the brown sugar melt into a sticky base that caramelizes perfectly under the cookie.
• Pineapple Rings (1 small can, cut into pieces): Adds juicy bursts of tropical flavor; fresh pineapple works beautifully too.
• Maraschino Cherries (halved): Brings that classic pop of color and sweetness right in the center of each cookie.

How to Make Pineapple Upside-Down Cookies

Step 1: Prepare the Cookie Dough

Start by preheating your oven to 350°F (175°C); lining your baking sheet with parchment paper or a silicone mat will prevent sticking and make cleanup a breeze. In a mixing bowl, cream together the softened butter and granulated sugar until they become light, fluffy, and almost cloud-like—this is the magic that leads to a tender cookie. Next, add the egg and vanilla extract, blending until smooth and glossy. Separately, whisk the flour, baking powder, and salt, then gradually fold these dry ingredients into your wet mix just until a soft dough forms—remember, the gentler the fold, the softer the cookie!

Step 2: Prepare the Topping

In a small bowl, combine the melted butter and brown sugar until they form a silky, caramel-like mixture. This will be the divine base of your topping that bubbles and caramelizes under the heat of the oven. Drop about one teaspoon of this mixture spaced evenly on your prepared baking sheet, leaving enough room for the cookies to spread comfortably as they bake.

Step 3: Assemble the Cookies

Now, place a small piece of pineapple or a few tidbits on top of each dollop of the brown sugar mixture—it’s the sweet heart of your cookie! Nestle a halved maraschino cherry right in the center of the pineapple for that iconic burst of color and fruity sweetness. Afterward, scoop roughly 1 ½ tablespoons of your cookie dough, gently flatten it, and place it over the pineapple and brown sugar base, pressing lightly so it covers the topping but seals around the edges. This sealing is key to keep the topping wonderfully intact as it bakes.

Step 4: Bake the Cookies

Slide the tray into the oven and bake for 12 to 15 minutes, or until the cookies turn a golden brown around the edges. The aroma will instantly tell you something special is happening! Once baked, allow the cookies to cool on the sheet for about 5 minutes. This resting time helps the caramelized topping firm up a little, making flipping easier without losing any of that gooey goodness.

Step 5: Serve and Enjoy

The final, most exciting step is flipping the cookies right side up to reveal the glistening pineapple and cherry tops, which look as stunning as they taste. These cookies shine as a sweet treat on their own but are so versatile they can be enjoyed anytime you crave a bite of tropical sunshine packed with nostalgic flavor.

How to Serve Pineapple Upside-Down Cookies

Garnishes

To accentuate the charm of your Pineapple Upside-Down Cookies, add a light dusting of powdered sugar or a small drizzle of honey for extra sweetness and a glossy finish. A dollop of whipped cream or a sprinkle of toasted coconut flakes adds beautiful texture and complements the tropical flair perfectly.

Side Dishes

Pair these cookies with a scoop of vanilla ice cream or a chilled pineapple sorbet for a refreshing contrast to the warm caramel topping. They also work wonderfully alongside a cup of strong coffee or a bright herbal tea, providing a sweet counterbalance to the bitterness or earthiness of your drink.

Creative Ways to Present

Serve your Pineapple Upside-Down Cookies on a rustic wooden board nestled amidst fresh pineapple leaves and sliced fruit for a vibrant, tropical display. You can even stack a few to build a mini “cookie cake” centerpiece at your gathering or place them individually in decorative cupcake liners for a charming touch that’s perfect for parties or gift-giving.

Make Ahead and Storage

Storing Leftovers

Keep your leftover Pineapple Upside-Down Cookies fresh by storing them in an airtight container at room temperature. They’ll stay soft and flavorful for up to 3 days, though they rarely last that long! If your kitchen is warm, a cool spot is best to avoid the caramel topping becoming overly sticky.

Freezing

You can freeze these cookies to enjoy later without losing any of their magic. Place cooled cookies in a single layer on a baking sheet and freeze until firm, then transfer them to a resealable freezer bag or airtight container. They’ll keep well for up to 2 months and make an easy, delightful treat whenever the craving strikes.

Reheating

When ready to enjoy frozen Pineapple Upside-Down Cookies, thaw them at room temperature for about 30 minutes, then warm briefly in a preheated 300°F (150°C) oven for 5 minutes to revive that fresh-baked softness and caramelized sweetness. Avoid the microwave if possible—it tends to soften the caramel too much and can make the cookies soggy.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple works wonderfully and adds a vibrant natural sweetness. Just be sure to cut it into small, evenly sized pieces so it bakes evenly and fits nicely on the cookie base.

What if I don’t have maraschino cherries?

No worries! Fresh cherries, dried cranberries, or even small pieces of red candied fruit can be great alternatives. They all add that lovely pop of color and a burst of sweetness to your cookies.

Are these cookies gluten-free?

They can be! Simply substitute the all-purpose flour with a 1:1 gluten-free baking flour blend. Make sure your baking powder is gluten-free as well, and your Pineapple Upside-Down Cookies will be safe for gluten-sensitive diets.

How do I make this recipe egg-free?

An easy swap is a flax egg: mix 1 tablespoon of ground flaxseed with 3 tablespoons of water, let it sit for a few minutes until gelled, then use it in place of the egg. This keeps the dough moist and binds the ingredients nicely.

Can I make these cookies larger or smaller?

You can definitely adjust the size depending on your preference! Just remember to adjust the baking time accordingly—smaller cookies will bake faster, while larger ones will need a bit more time. Keep an eye on their golden edges for the perfect doneness.

Final Thoughts

These Pineapple Upside-Down Cookies are a true joy to make and even more delightful to eat. With their buttery cookie base, caramelized topping, and bursts of fruity sweetness, they offer that classic, nostalgic flavor in a fun, portable form. I absolutely encourage you to give this recipe a try — once you do, they’re sure to become a favorite go-to treat that brightens your day with every bite!

Print