I can’t wait to share these Caramelized Pineapple Cookie Cups with you. They’re my tropical twist on traditional pineapple upside-down cake, but with a cookie dough shortcut that’ll save you tons of time. The gooey caramel, sweet pineapple rings, and buttery cookie base come together in perfect harmony. And don’t get me started on that maraschino cherry on top—it’s not just pretty, it’s the perfect tangy complement. Want to know my secret for making these irresistible treats even better?
Why You’ll Love these Caramelized Pineapple Cookie Cups
While you might think pineapple only belongs on pizza (controversial, I know), these cookie cups will change your mind forever. The magic happens when brown sugar caramelizes with butter, creating a sticky-sweet topping that seeps into every bite.
I’m obsessed with how the sugar cookie base stays soft in the middle but gets perfectly crisp around the edges. Plus, they’re ridiculously simple to make. No mixer required, no fancy techniques.
That bright maraschino cherry in the center? Not just pretty—it adds the perfect tartness to balance the sweetness. Trust me, these little treats deliver big tropical flavor.
What Ingredients are in Caramelized Pineapple Cookie Cups?
These caramelized pineapple cookie cups combine the convenience of store-bought cookie dough with the nostalgic flavors of a classic pineapple upside-down cake.
- 1 roll refrigerated sugar cookie dough
- 1/4 cup butter, melted
- 2/3 cup brown sugar
- 8 pineapple rings, drained (from canned pineapple)
- 8 maraschino cherries
For an extra burst of tropical flavor, you might want to keep some of that pineapple juice from the can—the recipe suggests drizzling a bit over the finished cookies for a more pronounced pineapple taste.
How to Make these Caramelized Pineapple Cookie Cups
Step 1: Preheat Your Oven
Preheat your oven to 350°F, giving it plenty of time to reach the proper temperature while you prep the other ingredients.
A fully preheated oven guarantees even baking and that perfect golden cookie texture.
Step 2: Prepare the Caramel Base
Mix 1/4 cup melted butter with 2/3 cup brown sugar until well combined.
This sweet, buttery mixture creates that signature caramelized flavor that makes these cookie cups so irresistible.
Step 3: Fill Muffin Cups
Spoon the butter and brown sugar mixture evenly into 8 muffin cups.
This will create the gooey, caramelized topping that becomes the bottom of your cookie cups once inverted—the magic of upside-down desserts.
Step 4: Add Pineapple and Cherries
Place one pineapple ring in each muffin cup, then nestle a maraschino cherry in the center of each ring.
These fruits create that classic pineapple upside-down cake look and provide sweet, fruity pops of flavor.
Step 5: Add Cookie Dough
Cut the roll of refrigerated sugar cookie dough into 8 equal slices and place one slice on top of each pineapple ring.
The dough doesn’t need to completely cover the pineapple yet—it’ll spread while baking.
Step 6: Bake to Perfection
Bake the cookie cups for 15-18 minutes until they’re beautifully golden brown.
You’ll know they’re done when the cookie part is set and the caramel mixture is bubbling around the edges.
Step 7: Cool Slightly
Allow the cookie cups to cool in the pan for about 5 minutes.
This cooling period is vital—too hot and they’ll fall apart, too cool and the caramel will stick to the pan.
Step 8: Invert and Serve
Carefully invert the muffin pan onto a serving plate to release the cookie cups.
For an extra burst of tropical flavor, consider drizzling a bit of the reserved pineapple juice over the tops before serving.
For best results, use a premium baking cookware set that distributes heat evenly and prevents sticking.
What to Serve with Caramelized Pineapple Cookie Cups
These delightful little treats are perfect for dessert, but why stop there? For an indulgent finishing touch, serve them slightly warm with a scoop of vanilla bean ice cream that melts beautifully into the caramel sauce.
A dollop of freshly whipped cream works wonderfully too, especially when paired with a cup of rich, dark coffee to balance the sweetness.
For brunch, these cookie cups shine alongside a tropical fruit salad with mango and kiwi.
If you’re feeling fancy, a coconut rum sauce drizzled over the top takes these to next-level territory.
And don’t underestimate how perfect these are with a cold glass of milk—sometimes the simplest pairings are the most satisfying!
Caramelized Pineapple Cookie Cups Substitutions and Variations
• Garnish Ideas: Finish with a light dusting of powdered sugar, a drizzle of salted caramel, or toasted macadamia nut pieces for extra crunch and flavor dimension.
Leftovers and Storage for these Caramelized Pineapple Cookie Cups
These delightful cookie cups taste best when enjoyed fresh from the oven while the caramelized topping is still warm and gooey.
But don’t worry if you have extras! Store leftovers in an airtight container in the refrigerator for up to 3 days.
Place parchment paper between layers to prevent sticking. For longer storage, these freeze beautifully for up to 1 month—just wrap each cup individually in plastic wrap first.
To refresh, warm refrigerated cookie cups in the microwave for 10-15 seconds or in a 300°F oven for about 5 minutes until just warmed through.
From frozen, thaw in the refrigerator overnight before reheating.
The caramel can make these treats soggy over time, so they’re definitely at their prime when freshly made.
A quick reheat restores much of that just-baked magic!
Final Thoughts
These Caramelized Pineapple Cookie Cups bring together the nostalgic charm of pineapple upside-down cake with the convenience of cookies. The magic happens when that buttery brown sugar transforms into a rich caramel that hugs each juicy pineapple ring, while the soft sugar cookie base provides the perfect contrast in texture. They’re ideal for potlucks or weekend family gatherings when you want something special without hours in the kitchen. With just a handful of ingredients and muffin tins you probably already have, these little treats deliver joy in each bite—proof that sometimes the most delightful desserts come in the smallest packages.
