Pineapple Upside Down Cookies Recipe

I absolutely love this Pineapple Upside Down Cookies Recipe because it captures all the nostalgic flavors of the classic pineapple upside down cake but in a delightful, handheld cookie form. It’s such a fun twist that works perfectly for parties, potlucks, or just when you want a little tropical sunshine in your kitchen. When I first tried making these, I was amazed at how the caramelized pineapple and cherry topping melded with the soft, buttery cookie base—it’s like a mini party in every bite!

You’ll find that these cookies come together quite easily, even if you’re new to baking. The cool part is that you prep the topping right in the muffin tin, so there’s no messy pan to clean later. Plus, the recipe has a nice balance of sweet, tangy, and buttery flavors that make it a standout. Trust me—you’re going to want to keep this Pineapple Upside Down Cookies Recipe in your baking rotation for years to come.

this …

Ingredients You’ll Need

These ingredients come together beautifully to give you that classic pineapple upside down flavor with a soft cookie base, plus the juiciness of pineapple and cherries that make these cookies so special.

• Butter: Use real butter, softened for the dough, and melted for the pineapple topping to get that rich, golden caramelization.
• Granulated Sugar: Sweetens the dough nicely without overpowering the pineapple topping.
• Egg: Helps bind the cookie dough and adds moisture.
• Vanilla Extract: Adds warmth and depth of flavor to the dough.
• Powdered Sugar: Contributes to the tender texture of the cookie.
• Vegetable Oil: Keeps the cookies soft and moist.
• Baking Soda: Gives just enough lift without toughening the cookies.
• Cream of Tartar: Helps stabilize the dough and adds tenderness.
• All Purpose Flour: The base of your cookie dough, giving structure.
• Pineapple Rings: Use well-drained canned pineapple for that authentic, juicy topping.
• Maraschino Cherries: Adds a pop of color and sweet cherry flavor at the center.
• Brown Sugar: For the topping caramel layer, providing rich molasses flavor and color.

Variations

I love how versatile this Pineapple Upside Down Cookies Recipe is. You can easily tweak it to match your tastes or dietary needs, making it a great base for experimenting.

• Gluten-Free: I’ve swapped all-purpose flour for a gluten-free blend with great results, perfect if you have gluten sensitivities.
• Vegan: Try replacing butter with coconut oil and using a flax egg instead of a regular egg for a plant-based version that’s still delicious.
• Spiced Twist: Adding a pinch of cinnamon or nutmeg to the cookie dough adds a warm, cozy flavor that I love in fall months.
• Fruit Swap: I sometimes sub in peach slices or berries instead of pineapple for a seasonal change that’s just as tasty.

How to Make Pineapple Upside Down Cookies Recipe

Step 1: Prepare Your Toppings

Start by preheating your oven to 350°F. Then, in a small bowl, combine the melted butter with brown sugar and mix them until smooth. Drain your pineapple rings very well—this step is crucial to avoid soggy cookies. Drop about one tablespoon of the buttery brown sugar mixture into each well of a muffin tin. Place a pineapple ring on top, then nestle a maraschino cherry right in the center. I learned early on that staggering the placement of these helps the cookies bake evenly and prevents them from sticking to one another as they spread.

Step 2: Make the Cookie Dough

In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy—don’t rush this part, scraping down the sides occasionally. Then add the egg and vanilla extract, mixing well for another 2-3 minutes. Slowly add the vegetable oil and powdered sugar, beating until you get a pale yellow, creamy dough. In a separate bowl, whisk together the flour, baking soda, and cream of tartar, then gradually add that to your wet ingredients, mixing just until combined. The cookie dough should feel soft but not sticky.

Step 3: Assemble and Bake

Using a cookie scoop (I use size #24), scoop out dough balls and press them flat with your palm into roughly 3-inch discs. Place each flattened dough disc on top of the pineapple ring and cherry in the muffin tin, gently pressing the dough into the sides of the well to seal in all that sweet goodness. Bake for 8-10 minutes, watching for the edges to become lightly golden and the centers to lose their glossy appearance. This is your sign that they’re perfectly baked—make sure not to overbake or they’ll dry out.

Step 4: The Big Flip Reveal

This is my favorite part! Once the cookies come out of the oven, immediately invert the muffin tin onto a parchment-lined cookie sheet. The cookies should fall out easily, revealing the gooey pineapple and cherry topping now gloriously displayed on top. Let them cool completely before serving or the topping can be a bit messy. I love how dramatic this flip is—it’s like the cookie version of the classic cake, but portable!

How to Serve Pineapple Upside Down Cookies Recipe

Garnishes

I like to dust these cookies with a little powdered sugar on top for an extra touch of sweetness and a pretty finish. Sometimes a light drizzle of melted white chocolate or a sprinkle of toasted coconut flakes can take them over the edge, especially if you’re serving for a special occasion.

Side Dishes

These cookies pair wonderfully with a big scoop of vanilla ice cream or a dollop of whipped cream. For a drink, my family loves serving them alongside a tropical punch or even a cup of freshly brewed coffee to balance the sweetness.

Creative Ways to Present

I’ve had fun arranging these Pineapple Upside Down Cookies Recipe on a pretty platter lined with banana leaves for summer parties, or stacking them in a tiered dessert tray for birthdays. Adding a few fresh pineapple slices and cherries around the platter makes the presentation look festive and inviting.

Make Ahead and Storage

Storing Leftovers

Store your cookies in an airtight container at room temperature—they’ll keep beautifully for up to a week. I find they taste best within the first 2-3 days when the pineapple is still juicy and the cookie remains soft, so plan to enjoy them fresh if you can!

Freezing

These cookies don’t freeze super well because the pineapple and cherry release a lot of water when thawed, making the texture a bit soggy. If you do freeze them, wrap individually in plastic wrap and place in a sealed freezer bag, then reheat gently to help firm them back up.

Reheating

To bring leftovers back to life, pop the cookies in a 300°F oven for about 5 minutes or warm them briefly in the microwave (about 15-20 seconds) just until the cookie is soft and the topping is slightly sticky again. This helps revive their fresh-baked charm.

FAQs

Final Thoughts

This Pineapple Upside Down Cookies Recipe holds a cozy spot in my heart because it brings back fond memories of sharing desserts with family and friends, but with a fresh, fun twist that feels so modern. Once you try making these, I’m confident you’ll want to bake them again and again for both everyday treats and festive occasions. So go ahead—grab that muffin tin, drain those pineapples well, and make some magic happen in your kitchen. You’re going to love showing off this sunny, sweet crowd-pleaser!

Print