If you love the sweet, caramelized flavor of pineapple upside‑down cake but want something handheld and fun, these Pineapple Upside‑Down Sugar Cookies are just the dessert to make. They take classic sugar cookies and pair them with the tropical brightness of pineapple and a hint of warm caramel‑like flavor — all in a soft, chewy cookie.
Perfect for summer gatherings, potlucks, or a weekend baking project, these cookies offer the best of both worlds: familiar sugar cookie texture with a fruity, slightly tangy twist. They’re soft in the middle, gently crisp around the edges, and topped with bits of juicy pineapple that give every bite a burst of flavor. Whether you’re baking with kids, preparing treats for guests, or craving something sweet with a twist, this recipe delivers warmth and nostalgia with a tropical touch.
Ingredients :
Below is the full list of ingredients you’ll need to make this batch of Pineapple Upside‑Down Sugar Cookies. Each ingredient is included for a reason — whether it adds structure, sweetness, moisture, or that classic pineapple character.
Dry Ingredients
- 2¾ cups all‑purpose flour
This forms the base of the cookie dough. Using all‑purpose flour gives structure while allowing the cookies to stay tender. - 1 teaspoon baking powder
Works with baking soda to give lift and a light texture. - ½ teaspoon baking soda
Helps the cookies rise and creates a tender crumb. - ½ teaspoon salt
Enhances flavor and balances sweetness.
Sugars
- 1 cup granulated sugar
Provides sweetness and contributes to the light, delicate texture of sugar cookies. - ½ cup packed brown sugar
Adds richness and moisture, and complements the pineapple’s caramel notes.
Fats & Eggs
- 1 cup unsalted butter, softened
Butter gives flavor and tenderness. Make sure it’s softened to room temperature for easy creaming. - 1 large egg + 1 egg yolk
Eggs add structure and moisture; the extra yolk ensures richness and chewiness.
Flavorings
Pineapple Topping
- ½ cup crushed pineapple, well drained
Use canned crushed pineapple and drain thoroughly. Excess juice can make the cookies soggy. - 2 tablespoons brown sugar (for pineapple topping)
Sprinkled on top of cookies before baking, this sugar caramelizes slightly with the pineapple.
Finishing Sugar
- Additional granulated sugar (about ½ cup)
For rolling the cookie dough balls before baking. It creates a light, crackled sugar coating that adds sparkle and texture.
Step‑by‑Step Directions :
Follow these steps carefully for soft, well‑flavored Pineapple Upside‑Down Sugar Cookies that bake up evenly and beautifully.
1. Preheat and Prepare
- Preheat your oven to 350°F (175°C).
- Line a baking sheet with parchment paper or a silicone baking mat. This prevents sticking and ensures even baking.
2. Mix Dry Ingredients
- In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
- Set this dry mixture aside — you’ll add it to the wet ingredients later.
3. Cream Butter and Sugars
- In a large mixing bowl, add the softened butter, granulated sugar, and brown sugar.
- Using a hand mixer or stand mixer, beat on medium speed for 2–3 minutes, until the mixture is light and fluffy.
- Scrape down the bowl once or twice so everything blends evenly.
4. Add Eggs and Extracts
- Crack in the egg and egg yolk, then add the vanilla extract.
- Mix on medium speed until combined and smooth.
- If you’re using pineapple or rum extract, add it now and blend briefly.
5. Combine Wet and Dry
- With the mixer on low speed, gradually add the dry flour mixture to the wet butter mixture.
- Mix until the dough just comes together and no streaks of flour remain.
- Don’t overmix — this keeps the cookies soft.
6. Form the Dough
- Scoop about 1½ tablespoons of dough and roll it into a ball between your palms.
- Roll each ball in the finishing granulated sugar so it’s coated evenly.
7. Prepare Pineapple Topping
- In a small bowl, mix the crushed pineapple with the 2 tablespoons of brown sugar.
- Pat the mixture gently with a paper towel to absorb any extra moisture.
8. Top the Cookies
- Place the sugar‑coated dough balls spaced about 2 inches apart on the prepared baking sheet.
- Press your thumb or the back of a spoon gently into each ball to make a shallow indention.
- Spoon a small amount (about ½–1 teaspoon) of the pineapple mixture into each indention.
- Try to keep the pineapple topping from overflowing onto the cookie base too much — this helps them bake evenly.
9. Bake to Perfection
- Bake in the preheated oven for 10–12 minutes, or until:
- The edges look set
- The underside is lightly golden
- The pineapple pieces are slightly caramelized
- Rotate the baking sheet halfway through for even baking.
10. Cool on the Tray
- Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack.
- This short rest helps them firm up and hold their shape.
Tips & Variations
Here are some ways to make this recipe even more delicious or tailored to your taste:
Add Warm Spices
- Sprinkle ½ teaspoon cinnamon or ¼ teaspoon ground ginger into the dry mix for a spicy‑sweet twist.
- Nutmeg pairs well with pineapple and brown sugar, giving a cozy warmth.
Make Them Extra Chewy
- Use an extra egg yolk or add another tablespoon of brown sugar — extra brown sugar means more chew.
Switch Up the Fruit
- Substitute pineapple with mango chunks or peach pieces for a seasonal version.
- Just drain fruit well so dough doesn’t get soggy.
Citrus Zest Kick
- Add a teaspoon of lemon or orange zest to the dough for a brighter citrus note that complements pineapple beautifully.
Chocolate Drizzle
- After cooling, drizzle with melted white or dark chocolate for a sweet and decorative finish.
Storage & Serving Suggestions
Storage
- At room temperature:
Place cookies in an airtight container for up to 3–4 days. - In the fridge:
For longer storage, keep them refrigerated for 1 week. - Freezing:
You can freeze baked cookies for up to 3 months. Thaw before serving.
Conclusion :
These Pineapple Upside‑Down Sugar Cookies are a joyful twist on two beloved classics — a cookie you can pick up and enjoy, and the signature pineapple caramel flavor of the upside‑down dessert you grew up with. They balance sweet, tangy fruit with soft, buttery cookie texture in every bite.
Whether you’re baking for a party, gifting friends, or making memories in your own kitchen, these cookies deliver comfort and brightness together. The process, while detailed, is straightforward and adaptable — giving you room to customize spices, add citrus zest, switch fruits, or turn up the sweetness as you like.
What makes this recipe special isn’t just the delicious final result — it’s also the way it brings together simple ingredients to create something memorable. With a spread of these at your next gathering, you’re sure to inspire smiles, compliments, and requests for the recipe.
So preheat that oven, gather your ingredients, and enjoy the sweet, tropical deliciousness of Pineapple Upside‑Down Sugar Cookies. Your kitchen will smell amazing, and everyone lucky enough to taste them will remember your effort and creativity.
