Can I use fresh pineapple instead of canned?

Absolutely! Just make sure to slice the fresh pineapple thinly and dry it very well before baking, since it has more natural juice than canned rings.

Do I really need to refrigerate these cookies?

Yes, for food safety and best texture. The fruit topping makes them perishable, but they stay beautifully soft and delicious in the fridge.

Can I make the dough ahead of time?

Definitely! Prepare the dough, cover, and refrigerate for up to two days. Let it sit at room temperature briefly before topping your fruit and baking.

My cookie dough is too sticky—what should I do?

If your dough feels sticky, refrigerate it for 20–30 minutes before forming into balls. This makes shaping and handling a breeze!

Pineapple Upside Down Cookies Recipe

Name: Pineapple Upside Down Cookies Recipe
Prep time: 15 min
Cook time: 25 min
Total time: 40 min
Cuisine: American
Ingredients: 2 (20-ounce) cans pineapple rings, drained; 9 maraschino cherries, halved; 1/2 cup brown sugar (about 1 1/2 teaspoons per ring for sprinkling); 1 cup unsalted butter, softened; 3/4 cup brown sugar; 1/2 cup granulated sugar; 2 large eggs; 1 teaspoon vanilla extract; 3 cups all-purpose flour; 1 teaspoon baking powder; 1 teaspoon baking soda; 1/2 teaspoon salt

If you’re craving a playful twist on a classic dessert but don’t have time for fussing over cakes, these Pineapple Upside Down Cookies are about to become your go-to treat. They pack all the tropical sweetness, buttery richness, and charming good looks of the beloved cake—only in a hand-held, palm-sized package. In just about 40 minutes, you’ll have a tray full of gooey, golden cookies, perfect for impressing guests, treating your family, or simply cheering up a busy weeknight. Yes, cookies this dazzling really are that easy!

Why You’ll Love This Recipe

Seriously Fast: The cookies go from pantry to plate in under an hour, so you don’t need to plan ahead or wait for things to cool for hours.
Incredibly Pretty: Each cookie looks like a little work of art, complete with a caramelized pineapple slice and a cheerful cherry on top.
Easy to Make: No fancy tools or techniques required—these cookies are wonderfully straightforward.
Familiar Flavors, Fun Format: They deliver pineapple upside down cake vibes in a soft, buttery cookie that’s a joy to eat and share.
Crowd-Pleaser: These are the kind of treats that never, ever last long—expect happy faces and requests for seconds!

Ingredients You’ll Need

This recipe keeps things simple, using familiar ingredients and a few smart techniques to create showstopping results.

Pineapple Rings: For that lush, tangy-sweet layer—dried well so your cookies bake up perfectly.
Maraschino Cherries: The classic center, adding a pop of color and a touch of nostalgia.
Brown Sugar: Gives that signature caramelized edge and even more depth in the cookie dough.
Unsalted Butter: The secret to super rich, tender cookies—use it at room temperature for easy mixing.
Granulated Sugar: Balances sweetness and ensures a delicate crumb.
Eggs: Help bind the dough for structure and softness.
Vanilla Extract: Brings gentle warmth and rounds out the flavors.
All-purpose Flour: The sturdy (but not heavy) base for these cookies.
Baking Powder & Baking Soda: The duo that ensures your cookies have just the right lift and chew.
Salt: Absolutely essential—for flavor balance and to keep things from tipping into “too sweet” territory.

Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Variations

These cookies are wonderfully adaptable, and you can truly make them your own:

Go Nutty: Sprinkle a bit of finely chopped pecans or walnuts on top of the brown sugar before adding your cookie dough.
Coconut Twist: Add a handful of shredded coconut to the dough or sprinkle on the pineapple for extra tropical flavor.
Cherry Switch-Up: Try swapping out maraschino cherries for fresh or dried cherries for a little tang.
Mini Cookies: Use pineapple tidbits instead of rings and make bite-sized cookies for parties or snacking.
Gluten-Free: Substitute a good 1-to-1 gluten-free flour blend for the all-purpose flour—these cookies are all about flavor!

How to Make Pineapple Upside Down Cookies

Step 1: Prep Your Pan and Fruit

Preheat the oven to 400°F (204°C). Line two baking sheets with parchment or silicone mats. Dry the pineapple rings thoroughly and arrange them spaced out on the prepared pans—a little less than a dozen per sheet. Nestle half a cherry in the center of each ring, then sprinkle each with a generous teaspoon or so of brown sugar.

Step 2: Caramelize the Pineapple

Pop the trays in the oven for about 10 minutes, just until the brown sugar bubbles and glazes the pineapple. Let the pans cool while you work on the dough.

Step 3: Make the Cookie Dough

Beat together soft butter, brown sugar, and granulated sugar until creamy, fluffy, and light in color—this is the base for that cake-like texture. Add eggs and vanilla, mixing until just combined.

Step 4: Add Dry Ingredients

Stir in the flour, baking powder, baking soda, and salt, mixing gently until no dry spots remain. Don’t overdo it; just mix until it’s evenly incorporated.

Step 5: Top the Pineapple and Bake

Scoop about two tablespoons of cookie dough, roll into a ball, and place it right on top of each pineapple ring, flattening gently so it hugs the fruit. Return the pans to the oven and bake for 12–14 minutes, until the cookie tops are golden brown.

Step 6: Cool and Enjoy!

Let the cookies cool on the pans for at least 15 minutes before serving warm for that classic gooey treat, or transfer to a wire rack to cool completely.

Pro Tips for Making the Best Cookies

Dry that Fruit: Take the time to blot the pineapple rings—extra moisture is the enemy of perfect cookies.
Fluffy Dough is Key: Creaming your butter and sugars until truly light and fluffy makes all the difference.
Gentle with Dough: When pressing the dough onto the pineapple, don’t smash it down. A gentle pat ensures a tender cookie.
Rotating Trays: If you use both oven racks, rotate the pans halfway for even browning.

How to Serve

Pineapple Upside Down Cookies are just delightful served still a little warm, when the caramelized pineapple and cherry are soft and gooey.

Dessert Platter: Arrange on a pretty tray with a dusting of powdered sugar or a scoop of vanilla ice cream for a decadent ending to any meal.
Afternoon Snack: Pair with coffee, iced tea, or even a refreshing sparkling water for a sweet pick-me-up.
Party Friendly: Pop them into cupcake liners for easy serving at gatherings and potlucks.
Brunch Spread: These cookies add a cheerful pop to a breakfast or brunch table alongside fruit and yogurt.

Make Ahead and Storage

Storing Leftovers

Because of the juicy fruit, refrigerate these cookies in an airtight container for up to 5 days. If you like them extra soft, let them sit at room temperature for 10 minutes before serving.

Freezing

Freeze fully baked cookies in a single layer, then transfer to a freezer bag for up to 2 months. Thaw in the fridge, then enjoy chilled or gently rewarm.

Reheating

To recapture that “just baked” magic, microwave individual cookies for 10–15 seconds, or warm in a low oven (300°F) for a few minutes.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Just make sure to slice the fresh pineapple thinly and dry it very well before baking, since it has more natural juice than canned rings.
Do I really need to refrigerate these cookies?

Yes, for food safety and best texture. The fruit topping makes them perishable, but they stay beautifully soft and delicious in the fridge.
Can I make the dough ahead of time?

Definitely! Prepare the dough, cover, and refrigerate for up to two days. Let it sit at room temperature briefly before topping your fruit and baking.
My cookie dough is too sticky—what should I do?

If your dough feels sticky, refrigerate it for 20–30 minutes before forming into balls. This makes shaping and handling a breeze!

Final Thoughts

Give these Pineapple Upside Down Cookies a try and discover a cookie that’s as joyful to look at as it is to eat. They’re fuss-free, bursting with sunshiny flavor, and just the thing for busy days or whenever you want to make something extra special without extra effort. Roll up your sleeves, have some fun, and enjoy every sweet, soft bite!