Pineapple Upside Down Sugar Cookies — Crowd-Pleasing

Bright, syrupy pineapple rings caramelize on top of buttery sugar-cookie dough — Pineapple Upside Down Sugar Cookies sing like summer in every bite. I developed this version after testing the method eight times to get a crisp, glossy pineapple top without soggy dough beneath. The technique borrows the caramel pan trick from classic upside-down cakes and adapts it for small, even cookies that bake quickly and plate beautifully. This is the cookie I perfected while teaching holiday bake-alongs; it’s forgiving and fast, and it travels well for potlucks. Read on for a complete ingredient breakdown, exact timings, and professional tips that keep the pineapple glossy and the cookies tender. If you want a shorter version of the idea, try this related pineapple upside-down sugar cookies for a slightly different take.

Why This Recipe Works

Caramelized pineapple syrup creates a shiny topping that locks in flavor while adding moisture to the cookie surface.
A higher butter-to-flour ratio yields tender, melt-in-your-mouth cookies rather than cake-like rounds.
Chilling the dough firms the fat, preventing spread and keeping pineapple slices centered.
Baking on parchment with a light sugar layer gives a crackling caramel edge without burning.
Using crushed pineapple juice for part of the liquid deepens pineapple flavor without over-wetting the dough.

Ingredients Breakdown

All-purpose flour 300 g (2 1/2 cups): Provides structure. Measure by weight for consistent results.
Baking powder 6 g (1 1/2 tsp): Gives a soft lift. Don’t substitute with baking soda alone.
Kosher salt 5 g (1 tsp Diamond Crystal; use 1/2 tsp if using Morton’s): Balances sweetness.
Unsalted butter 226 g (1 cup), softened: The primary fat for tenderness and flavor. Use real butter, not margarine.
Granulated sugar 200 g (1 cup): For sweetness and a crisp edge; for a browner look, swap 50 g (1/4 cup) with light brown sugar.
Egg 1 large (50 g): Binds and gives structure; room temperature for even mixing.
Pure vanilla extract 10 ml (2 tsp): Rounds the flavors.
Crushed pineapple, drained 120 g (1/2 cup) plus 60 ml (1/4 cup) reserved juice: The crushed fruit is folded into the topping syrup and the juice replaces part of the liquid for a deeper pineapple note. Drain well to avoid soggy dough.
Pineapple rings, canned, drained and patted dry — about 12 small rings or slices: Use rings that fit your cookie size. Fresh pineapple can be used but will require a shorter caramel time.
Brown sugar (for topping) 60 g (1/3 cup packed): Caramelizes under the pineapple.
Lemon zest 1 tsp (optional): Brightens the pineapple.
Optional: 30 g (1/4 cup) chopped toasted macadamia nuts or macerated cherries for placement in the center.

Substitutions and impact warnings:

Gluten-free: Use a tested 1:1 GF flour blend and add 1/2 tsp xanthan gum; texture will be slightly crumbly.
Dairy-free: Replace butter with a solid vegan butter stick; cookies will spread slightly more.
Egg substitute: Use 60 g (1/4 cup) unsweetened applesauce — expect a slightly cakier texture.

If you prefer a simpler pineapple cookie, compare this to a different take on the idea with these pineapple upside down cookies for inspiration.

Essential Equipment

Baking sheets (two), rimmed — for even heat.
Parchment paper or silicone baking mat — prevents sticking and eases cleanup.
2-inch round cookie cutter or 1 3/4–2-inch biscuit cutter — to size cookies for pineapple rings.
Small saucepan — to make the caramel pineapple syrup.
Cooling racks — for rapid cooling and crisp bottoms.
Digital scale — strongly recommended for accuracy.
Mixing bowls and a hand mixer or stand mixer with paddle attachment. If you don’t have a mixer, a sturdy wooden spoon works; beat the butter well to incorporate air.
Small offset spatula — helps spread caramel evenly under pineapple slices.

If you lack a 2-inch cutter, press dough into small rounds by hand for consistent size.

Prep Time: 20 minutes | Cook Time: 12 minutes per batch | Inactive Time: 30 minutes chilling | Total Time: about 1 hour (including cooling) | Servings: 24 cookies (1 cookie each)

Step 1: Make the Pineapple Caramel

In a small saucepan, combine 60 g (1/3 cup) brown sugar and 30 g (2 tbsp) unsalted butter over medium heat. Stir until sugar dissolves and the mixture is syrupy, about 2–3 minutes, bubbling gently. Remove from heat and stir in 60 ml (1/4 cup) reserved crushed pineapple juice and 1 tsp lemon zest; cool to warm, about 5 minutes.

Step 2: Prepare Dry Ingredients

Whisk together 300 g (2 1/2 cups) all-purpose flour, 6 g (1 1/2 tsp) baking powder, and 5 g (1 tsp) kosher salt in a medium bowl. Set aside. This ensures even leavening and prevents lumps.

Step 3: Cream Butter and Sugar

In a mixer, cream 226 g (1 cup) unsalted butter and 200 g (1 cup) granulated sugar on medium speed for 2–3 minutes until pale and fluffy; scrape the bowl once. Add 1 large egg and 10 ml (2 tsp) vanilla and beat until combined, about 30 seconds. Do not overmix after adding flour.

Step 4: Combine Wet and Dry

Add half the dry ingredients to the butter mixture and mix on low until just combined, about 15–20 seconds. Add 60 ml (1/4 cup) crushed pineapple (drained) and the remaining dry ingredients; mix until no dry streaks remain, about 10–15 seconds. Stop as soon as the dough looks uniform.

Step 5: Chill the Dough

Turn dough onto plastic wrap, press into a disk, and chill for 20–30 minutes until firm. Chilling firms the butter so cookies hold their shape and prevents pineapple from weighing them down. If you’re short on time, chill for at least 15 minutes.

Step 6: Shape Cookies and Add Pineapple

Preheat oven to 180°C (350°F). Line baking sheets with parchment. Roll dough to 6 mm (1/4 inch) thickness and cut 24 rounds with a 2-inch cutter. Place rounds on the sheet 2.5 cm (1 inch) apart. Spoon 1 tsp of the cooled pineapple caramel onto each round and spread gently to a 1 1/2-inch circle. Top each with a small pineapple ring or slice, pressing lightly so it adheres. If using, sprinkle chopped macadamia or a flake of sea salt.

Step 7: Bake

Bake at 180°C (350°F) for 10–12 minutes, rotating pans halfway through, until edges are golden and centers set. The tops should be glossy but not boiling. Remove from oven and let cool on pan for 5 minutes, then transfer to a cooling rack to cool completely.

Step 8: Finish and Store

Once cool, the pineapple top will be set and shiny. If you like a stronger caramel, brush lightly with an additional 5–10 g (1 tsp) warmed brown sugar syrup. Store cooled cookies in an airtight container at room temperature for up to 3 days.

Expert Tips & Pro Techniques

Chill the dough: Firm dough resists spread. Chill at least 20 minutes; overnight chill deepens flavor.
Drain pineapple very well: Excess juice causes soggy cookies. Pat slices dry with paper towels for 1–2 minutes.
Common mistake: burning the caramel. Cook on medium heat and remove as soon as it glazes; carryover heat will finish the gloss.
Make-ahead: Bake the cookies, cool completely, then freeze in a single layer on a tray. Transfer to a freezer bag for up to 2 months.
Professional trick for even tops: Spoon caramel into a small ring mold on each cookie, then place pineapple inside the ring so syrup stays under the fruit.
Lighter swap: Reduce butter by 30 g (2 tbsp) and add 15 g (1 tbsp) Greek yogurt; texture stays tender but slightly less rich. For more light-eating recipe ideas, see this roundup of natural weight-loss recipes that work.

Storage & Reheating

Refrigerator: Store in an airtight container for up to 5 days. Place parchment between layers to prevent sticking.
Freezer: Freeze baked, cooled cookies in a single layer on a tray for 1 hour, then transfer to a freezer-safe bag for up to 2 months. Thaw overnight in the fridge or at room temperature for 1–2 hours.
Reheating: Reheat in a 175°C (350°F) oven for 5–7 minutes to refresh crisp edges. Avoid microwaving — it makes the dough soggy and the caramel gummy.

Variations & Substitutions

Gluten-Free Version: Replace 300 g (2 1/2 cups) all-purpose flour with 330 g (2 1/2 cups) 1:1 GF blend and add 1/2 tsp xanthan gum. Bake 11–13 minutes.
Tropical Twist: Fold 30 g (1/4 cup) shredded coconut into the dough and top pineapple with 15 g (2 tbsp) toasted coconut before baking. Flavor deepens; bake time unchanged.
Cherry-Pineapple: Add a maraschino cherry or a spoonful of macerated cherry into the center of the pineapple ring. Use 20 g (1 tbsp) of cherry syrup in the caramel.
Vegan Option: Use 226 g (1 cup) vegan butter and an egg substitute (60 g/1/4 cup applesauce). Texture will be slightly more tender; bake 11–13 minutes.
Mini Cookies: Make 1-inch cookies with smaller pineapple rounds; reduce bake time to 8–10 minutes.

For a fruity swap that leans more tart, try adapting the topping ideas used in this raspberry sugar cookies recipe.

Serving Suggestions & Pairings

Serve warm with a dollop of whipped cream or coconut cream for contrast.
Pair with black tea or a citrusy sparkling wine for brunch.
For a savory-sweet board, offer with ham sliders or our toasted avocado and feta on toast — the salty-sour notes balance the cookies’ sweetness: avocado feta toast delight.
Gift idea: Stack cookies in a cellophane bag with a ribbon; include a note to reheat briefly.

Nutrition Information

Per serving: 1 cookie — recipe makes 24 cookies.

Calories: 160 kcal
Total Fat: 8 g
Saturated Fat: 4.5 g
Cholesterol: 25 mg
Sodium: 95 mg
Total Carbohydrates: 20 g
Dietary Fiber: 0.7 g
Sugars: 11 g
Protein: 2 g

Nutrition values are estimates. Actual values may vary based on specific ingredients and preparation methods.

Frequently Asked Questions

Q: Why did my cookies turn out flat and greasy?
A: Most likely the dough was too warm. Chill the dough at least 20–30 minutes so the butter firms and cookies hold shape. Also measure flour by weight.

Q: Can I make these without eggs?
A: Yes. Replace the single egg with 60 g (1/4 cup) unsweetened applesauce or a commercial egg replacer. Expect a slightly cake-like texture.

Q: Can I double this recipe for a party?
A: Yes. Double all ingredients and portion on multiple baking sheets. Bake in batches; do not crowd pans or the temperature will dip and cookies will spread.

Q: Can I prepare these the night before?
A: Absolutely. Shape and chill cut cookies overnight on a tray covered lightly with plastic wrap. Bake the next day straight from the fridge, adding 1 minute to bake time if still very cold.

Q: How long will these keep in the fridge?
A: Baked cookies keep up to 5 days in an airtight container in the refrigerator. For best texture, bring to room temperature before serving or reheat briefly.

Q: Can I use fresh pineapple instead of canned?
A: Yes. Pat slices dry and briefly sauté them in 1 tbsp brown sugar to release juice and caramelize slightly, 1–2 minutes per side. Reduce added pineapple juice in the caramel by half to avoid excess moisture.

Q: My pineapple top looks dull after baking. How do I fix that?
A: Brush lightly with 5–10 g (1 tsp) warmed brown sugar syrup or simple syrup while still warm. That restores shine without adding much sweetness.

Conclusion

These Pineapple Upside Down Sugar Cookies bring a bit of show-stopping shine to any dessert table, balancing crisp caramel, bright pineapple, and tender cookie dough. For another small-cookie approach to the same concept, try this Pineapple Upside Down Sugar Cookies that uses a slightly different caramel technique. If you love the caramelized pineapple flavor but want a classic single-layer dessert, this Buttery Pineapple Upside Down Cake Recipe shows how the same flavor sings in a cake format. Enjoy baking, and remember the best cookies come from precise measuring and gentle hands.