If you’re craving a nostalgic treat with a fruity, tropical flair, these pineapple upside-down sugar cookies are just the thing. They combine the buttery caramel flavor of classic pineapple upside-down cake with the chewy texture of a sugar cookie—all in a single, handheld dessert.

Best of all, this recipe is ideal for a wide range of dietary preferences. You’ll love how simple these are to make and how stunning they look fresh out of the oven. Also, it’s packed with vitamin C and anti-inflammatory compounds.

Table of Contents

Why You’ll Love Pineapple Upside-Down Sugar Cookies

🍍 Tropical and buttery flavor combo

🎉 Perfect for holidays, BBQs, or gifting

👩‍🍳 Beginner-friendly recipe with simple ingredients

🔁 Easy to customize with fun variations

Ingredients You’ll Need

For the Cookie Dough:

¾ cup unsalted butter, softened
1 cup granulated sugar
1 egg
1½ tsp vanilla extract
2 cups all-purpose flour
½ tsp baking powder
½ tsp baking soda
¼ tsp salt

For the Topping:

½ cup light brown sugar
3 tbsp melted butter
Pineapple rings (fresh or canned, drained and patted dry)
Maraschino cherries (optional)

Step-by-Step Instructions

1. Prepare the Dough

In a large bowl, cream butter and sugar until light and fluffy.
Add egg and vanilla; mix well.
In another bowl, whisk flour, baking powder, soda, and salt.
Gradually combine dry with wet ingredients until soft dough forms.
Chill dough for 20–30 minutes if sticky.

2. Preheat and Prep the Pan

Preheat oven to 350°F (175°C).
Line baking sheet with parchment or silicone mat.

3. Create the Caramel Base

In a small bowl, mix brown sugar and melted butter.
Spoon a small circle of this mixture onto the baking sheet.
Place a pineapple ring on top of each caramel spot.
Add a cherry in the center if using.

4. Add the Dough

Scoop dough (1.5–2 tbsp) and flatten slightly into discs.
Place one disc over each pineapple ring and gently press.
Make sure the dough covers the fruit but isn’t too thin.

5. Bake and Flip

Bake for 12–14 minutes, or until edges are golden.
Let cool on tray for 3–5 minutes.
Carefully flip cookies over while still warm to reveal the caramelized pineapple top.

Expert Tips for Perfect Results

Use room-temperature butter for easy creaming
Pat pineapple dry to prevent soggy bottoms
Don’t skip the chill if your dough is too soft
Slightly underbake for a chewy center
Use parchment paper or a silicone mat to prevent sticking

Flavor Variations to Try

🥥 Coconut-Pineapple: Add ½ cup shredded coconut to dough

🍑 Peach Upside-Down Cookies: Swap pineapple for thin peach slices

🍫 Pineapple-Chocolate Chip: Fold mini chips into dough for a fun twist

🌿 Spiced Dough: Add a dash of cinnamon, cardamom, or lemon zest

🧁 Mini Versions: Use muffin tins to shape individual cookie cups

Storage & Make-Ahead Tips

The beauty of these cookies is that they’re just as enjoyable the next day—and with the right storage, they stay soft, chewy, and delicious for days. Whether you’re prepping ahead or saving leftovers, here’s how to do it right.

📦 Room Temperature Storage

Perfect for short-term snacking, gift-giving, or make-ahead batches.

Store cooled cookies in an airtight container
Layer with parchment or wax paper to prevent them from sticking together
Keep them in a cool, dry place for up to 5 days

💡 Tip: Add a slice of white bread or a piece of apple inside the container to help keep the cookies soft longer!

❄️ Freezer Instructions

Want to make a batch for later? These cookies freeze beautifully both raw and baked.

✅ To Freeze Baked Cookies:

Let cookies cool completely
Layer between parchment and place in a freezer-safe container or zip-top bag
Freeze for up to 2 months

🕒 When ready to enjoy, reheat in a 300°F (150°C) oven for 5–6 minutes or until warm and soft.

✅ To Freeze Unbaked Dough:

Scoop dough into balls
Flash freeze on a baking sheet for 30–60 minutes
Transfer to a freezer bag and label with date
Freeze for up to 3 months

🧁 Pro Tip: Bake frozen dough balls directly from the freezer—just add 2–3 extra minutes to the baking time.

🔁 Fresh-Baked Feel Anytime

To revive baked cookies, simply:

Warm in the oven for a few minutes
Or microwave for 8–10 seconds (watch closely!)

The caramel topping will soften and the center will taste fresh from the oven.

Common Mistakes to Avoid

❌ Using wet pineapple – leads to soggy cookies

❌ Skipping parchment – caramel will stick!

❌ Overbaking – removes chewiness

❌ Overmixing – toughens the dough

🎯 Fix: Drain your fruit, chill the dough if sticky, and monitor the oven closely.

Nutrition & Portion Guide

Calories: Approx. 160 per cookie
Yield: 12–16 cookies depending on size
For smaller batches: halve recipe, or freeze extra dough
Lighten up with coconut sugar or plant-based butter

Creative Uses for Leftovers

Have a few extra cookies on hand? Don’t just eat them plain—transform them into showstopping mini desserts or flavorful add-ins with these easy ideas.

1. Crumble into Yogurt Parfaits

Layer crumbled cookies with Greek yogurt, chopped pineapple, and honey.
Perfect for breakfast, brunch, or an elegant afternoon snack.

2. Add to Ice Cream Sundaes

Use warm cookie chunks as a topping for vanilla, coconut, or caramel ice cream.
Drizzle with pineapple syrup or butterscotch for extra indulgence.

3. Use as a Base for Mini Cheesecakes

Press cookie crumbles into muffin cups as a crust, add your favorite cheesecake filling, and bake.
Top with pineapple slices or a cherry for that classic upside-down flavor in cheesecake form.

4. Chop and Layer into Fruit Trifles

Alternate layers of chopped cookie, whipped cream, and fruit (like strawberries or pineapple) in individual jars or a large trifle dish.
It’s quick, gorgeous, and irresistibly good.

💡 Bonus Tip: Store crumbled cookies in an airtight jar and use as a crunchy topping for oatmeal or smoothie bowls!

Frequently Asked Questions (FAQs)

These pineapple-topped sugar cookies may look fancy, but they’re actually super simple to customize. Here are answers to the most common questions to help you bake them with confidence.

🍍 Can I use fresh pineapple instead of canned?

Yes! Fresh pineapple works beautifully in this recipe.

Slice the pineapple into thin rings or half-moons so they bake evenly.
Make sure to remove the core for tenderness.
Most importantly, pat the slices completely dry with a paper towel to avoid soggy caramelization on the bottom.

💡 Tip: If your fresh pineapple is very juicy, roast it briefly in the oven to concentrate the flavor and remove moisture.

🌾 Can I make them gluten-free?

Absolutely! These cookies adapt well to gluten-free baking.

Use a 1:1 gluten-free flour blend that includes xanthan gum.
Check that your baking powder and other baking ingredients are certified gluten-free.
The texture may be slightly more delicate, but they’ll still be delicious and chewy.

💡 Bonus: Let the gluten-free dough chill slightly longer for easier handling.

🥥 Can I make them dairy-free?

Yes—this recipe can be made entirely dairy-free with a few easy swaps.

Use plant-based butter (like Earth Balance or Miyoko’s)
Replace the egg with a flax egg (1 tbsp flaxseed + 3 tbsp water)
Check your sugar to ensure it’s vegan-friendly if needed

✨ The final result will still be soft, sweet, and completely dairy-free.

🍒 What can I use instead of maraschino cherries?

Maraschino cherries are classic, but you can absolutely get creative:

Fresh cherries, halved and pitted
Dried cranberries or tart cherries
Raspberries for a pop of color and tang
Or simply skip them for a minimalist, pineapple-only version

💡 Flavor idea: Add a little chopped crystallized ginger in place of the cherry for a spiced twist!

🧁 Can I bake these in muffin tins?

Yes, and it’s a fantastic idea!

Muffin tins help the cookies hold a perfect round shape
They also capture extra caramel around the fruit
Grease each cup or line with parchment rounds for easy release

🧁 These mini cookie cakes are perfect for gifting or brunch spreads.

🍪 How do I keep the cookies soft after baking?

Keeping them soft is easy with a few tricks:

Slightly underbake the cookies so they stay chewy in the center
Store in an airtight container as soon as they’ve fully cooled
Add a slice of white bread or apple to the container to keep moisture inside
For longer freshness, store at room temp (up to 5 days) or freeze with parchment between layers

💡 Warm them for a few seconds in the microwave to restore that freshly baked softness anytime.

Final Thoughts

These pineapple upside-down sugar cookies are more than just a dessert—they’re a conversation starter, a nostalgic nod to a beloved classic, and a tropical twist that brings sunshine to every bite. From the buttery sugar cookie base to the glossy, caramelized pineapple topping, each element is crafted for maximum joy with minimum fuss.

Whether you’re:

Hosting a summer BBQ
Putting together a whimsical dessert tray
Sharing edible gifts with friends
Or simply baking something sweet for yourself

…this recipe checks all the boxes: fun to make, gorgeous to serve, and incredibly delicious to eat.

What’s more, it fits beautifully into a variety of dietary needs. And with all the ways to repurpose leftovers or get creative with flavors (hello, peach and coconut versions!), this is a cookie recipe you’ll come back to again and again.

So go ahead—grab your pineapple rings, warm up your oven, and get ready to flip your cookie game upside down. 🍍✨