Pineapple Upside Down Sugar Cookies bring the tropical nostalgia of a classic pineapple upside-down cake into a crisp, hand-held cookie, and Pineapple Upside Down Sugar Cookies are the perfect treat when you want bright flavor in every bite. If you love the caramelized pineapple-and-butter combo but want something smaller and shareable, this cookie version hits the mark—soft, buttery sugar cookies topped with a sweet pineapple ring and a light sprinkle of sugar. For another pineapple-forward dessert idea that’s easy to make ahead, you might enjoy these mini pineapple upside-down cheesecakes which pair the same flavors with a creamy filling.

Why make this recipe

Pineapple Upside Down Sugar Cookies are a clever mashup that brings bold, sunny flavors to familiar sugar cookies. They’re festive enough for parties and simple enough for an afternoon baking session with kids. The cookies are portable, customizable, and deliver the sweet tang of pineapple without the fuss of making a whole cake. Because the pineapple rings sit right on top during baking, each cookie gets a hint of caramelized fruit and a pretty presentation that feels special.

These cookies work well for potlucks, bake sales, picnics, and holiday platters. They also make a thoughtful homemade gift: stack them in a box with parchment paper, and you’ve got an eye-catching surprise that tastes as good as it looks.

How to make Pineapple Upside Down Sugar Cookies That Delight Every Bite

This recipe is straightforward: make a classic sugar cookie dough, portion it, place a well-drained pineapple ring on top of each portion, sprinkle a little sugar, and bake until golden. The pineapple softens and caramelizes slightly on top, while the cookie underneath stays tender. Use a cookie scoop for uniformity and a silicone baking mat or parchment to prevent sticking. If you want to speed things up, chill the dough for 15–20 minutes rather than an hour—chilling helps the cookies hold their shape but short chilling still gives great results.

Ingredients :

1 cup unsalted butter (softened), 1 cup granulated sugar, 1 large egg, 1 teaspoon vanilla extract (optional), 2 cups all-purpose flour (or gluten-free blend), 1 teaspoon baking soda, 1/2 teaspoon salt, 1 can canned pineapple rings (well-drained), 2 tablespoons additional sugar for sprinkling

Ingredient notes and swaps

Unsalted butter: Using unsalted butter lets you control sodium. If you only have salted, omit or reduce the added salt. For dairy-free, use a stick of vegan butter.
Flour: A 1:1 gluten-free baking blend usually works, but check the package for xanthan gum—if your blend doesn’t include it, add 1/4 tsp per cup for better texture.
Pineapple: Drain the canned pineapple thoroughly and pat rings dry with paper towels so cookies don’t become soggy. Reserve the juice for smoothies or a glaze.
Vanilla: Optional but recommended for depth. Try almond extract for a nutty twist (use half the amount).

Directions :

Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone mats and set aside.
Drain the canned pineapple rings very well. Pat them dry with paper towels and cut them into halves or quarters if you prefer smaller cookie toppers; whole rings work beautifully for medium cookies.
In a large bowl, cream together the softened unsalted butter and 1 cup granulated sugar until light and fluffy—about 2–3 minutes with an electric mixer on medium speed.
Beat in the large egg and 1 teaspoon vanilla extract (if using) until combined.
In a separate bowl, whisk together the 2 cups all-purpose flour, 1 teaspoon baking soda, and 1/2 teaspoon salt.
Gradually add the dry ingredients to the wet mixture, mixing on low speed until a soft dough forms. The dough should be slightly sticky but manageable; add a tablespoon of flour if it seems excessively sticky.
Use a 1.5 tablespoon cookie scoop (or roll 1–1.5 tablespoon portions) and place the dough balls about 2 inches apart on the prepared baking sheets.
Flatten each dough ball gently with the palm of your hand or the bottom of a glass to create a small well in the center to support the pineapple piece.
Place a well-drained pineapple ring piece on top of each flattened dough portion. If using whole rings, gently press them into the dough so they adhere but not so far that they sink completely.
Sprinkle each pineapple-topped cookie with a light dusting of the 2 tablespoons additional sugar.
Bake for 10–14 minutes, rotating the baking sheets halfway through. Cookies are done when the edges are set and the bottoms are lightly golden; the pineapple will be slightly caramelized.
Allow cookies to cool on the baking sheet for 3–5 minutes, then transfer to a wire rack to cool completely. Serve warm or at room temperature.

Pro Tips for Success Pineapple Upside Down Sugar Cookies That Delight Every Bite

Dry the pineapple thoroughly: Excess juice causes spreading and sogginess. Pat each slice or piece with paper towels before topping the cookie.
Use room-temperature butter and egg: They mix more evenly, creating a smoother, tender cookie texture.
Don’t over-flatten the dough: Create a shallow well for the pineapple but leave enough dough edge so the cookie bakes up around the fruit.
Watch the first batch closely: Oven temperatures vary—aim for slightly golden edges rather than deep browning.
Chill for thicker cookies: If you want thicker cookies with less spread, chill scooped dough for 20–30 minutes before topping with pineapple.
Space cookies well: Pineapple adds weight and moisture; give cookies at least 2 inches of space so they don’t merge while baking.

Flavor Variations Pineapple Upside Down Sugar Cookies That Delight Every Bite

Brown sugar and cinnamon: Replace half the granulated sugar in the dough with light brown sugar and add 1/2 teaspoon ground cinnamon for a warm, caramel-like flavor.
Coconut-lime twist: Roll cookie dough balls lightly in shredded sweetened coconut before flattening, and zest 1 lime into the dough for tropical brightness that pairs with pineapple.
Maple and pecan: Add 1 tablespoon pure maple syrup to the dough and sprinkle chopped toasted pecans around the pineapple for crunch and deeper sweetness.
Rum-free glaze: If you want a glaze reminiscent of rum flavor without alcohol, brush a tiny drizzle of pineapple juice mixed with a touch of lemon juice and powdered sugar over warm cookies after baking.
Chocolate-dipped edges: Once cookies are cool, dip half of each cookie’s edge into melted dark or milk chocolate and let set for a sweet contrast.

Serving Suggestions Pineapple Upside Down Sugar Cookies That Delight Every Bite

Party platter: Arrange cookies on a large platter with fresh mint sprigs and extra pineapple wedges for a tropical-themed spread.
Afternoon tea: Serve with a cup of black tea or a citrus green tea—the fruity cookies pair well with bright, slightly astringent brews.
Ice cream sandwich: Split a cookie, add a scoop of vanilla or coconut ice cream, and gently press into another cookie for a festive mini sandwich.
Dessert bar: Put cookies out alongside bites of fresh fruit, toasted coconut, and macaroons for a DIY tropical dessert bar.
Gift box: Stack cookies between parchment squares in a decorative tin or box. Tie with twine and add a handwritten tag for a lovely homemade gift.

Storage and Freezing Instructions Pineapple Upside Down Sugar Cookies That Delight Every Bite

Room temperature: Store cooled cookies in an airtight container at room temperature for up to 3 days. Place parchment between layers to keep them from sticking.
Refrigeration: Because of the pineapple, refrigeration helps extend freshness. Store airtight in the fridge for up to 1 week. Bring to room temperature before serving for the best texture.
Freezing: To freeze, place cooled cookies on a baking sheet in a single layer and freeze until solid (about an hour). Transfer frozen cookies to a freezer-safe bag or container with parchment between layers. Freeze for up to 3 months. Thaw on the counter for 30–60 minutes before serving.
Tip for reheating: Warm cookies for 5–10 seconds in the microwave or 3–4 minutes in a 325°F (165°C) oven to refresh the texture—watch closely so pineapple doesn’t overcook.

Nutrition Facts (Per Serving) — approximate (1 cookie)

Calories: 160 kcal
Protein: 1.4 g
Carbohydrates: 21 g
Fat: 7.7 g
Fiber: 0.4 g
Sodium: 100 mg

Nutrition note: These values are estimated using typical ingredient data and assuming the recipe yields about 24 cookies. Exact nutrition depends on factors like the size of your cookies, the drained weight of the pineapple can, and specific brands. If you need precise numbers for medical or dietary reasons, measure your ingredients and use a nutrition calculator or app.

FAQ About Pineapple Upside Down Sugar Cookies That Delight Every Bite

Can I make these cookies gluten-free?

Yes—swap the 2 cups of all-purpose flour for a cup-for-cup gluten-free baking blend that includes xanthan gum or add 1/4 teaspoon per cup of xanthan gum if your blend lacks it. The texture may be slightly different—gluten-free dough can be a bit more fragile—so chill the dough for 20–30 minutes, which helps it hold shape. Taste for seasoning since some gluten-free flours absorb more liquid; you might need a tablespoon of extra liquid (milk or dairy-free milk) if the dough feels crumbly.

How many cookies does this recipe make?

Yield depends on how large you portion the dough. Using a 1.5-tablespoon scoop typically produces about 24 medium cookies. If you make larger, whole-ring-topped cookies, you might get closer to 12–16. For smaller bite-size cookies using pineapple pieces, plan for 30–36. Adjust baking time accordingly—smaller cookies need less time, larger ones need a few extra minutes.

Can I use fresh pineapple instead of canned?

Yes, but fresh pineapple contains more juice and may need extra draining and patting dry to avoid soggy cookies. Slice and blot fresh pineapple pieces thoroughly; you can also briefly sauté the pieces in a tablespoon of butter and 1–2 teaspoons sugar to remove extra moisture and caramelize them slightly before topping the cookies. Keep in mind that fresh pineapple may brown faster, so watch baking time.

My pineapple rings make the cookies soggy — how do I prevent that?

Thorough draining and patting dry are essential. After draining the canned fruit, lay rings on paper towels and press gently to remove extra syrup. If using whole rings, consider cutting them into halves or quarters—smaller pieces transfer less liquid and sit better on top of the dough. Also, slightly flattening the cookie to create a well helps the dough bake around the fruit rather than under it, which reduces sogginess.

Can I make the dough ahead of time?

Absolutely. You can make the dough, wrap it tightly, and refrigerate for up to 48 hours before scooping and baking. Chilled dough actually performs well and produces thicker cookies with less spreading. You can also freeze scooped dough balls on a sheet tray until solid then store them in a bag; bake from frozen, adding a minute or two to the baking time.

Is there a way to make these cookies less sweet?

Yes—reduce the sugar in the dough by up to 25% (use 3/4 cup sugar instead of 1 cup) for a less sweet base. You can also use crushed fresh pineapple pieces sparingly and skip the 2 tablespoons of extra sugar on top, or substitute that sprinkle with a light dusting of finely grated coconut for texture instead of added sweetness. Using unsweetened or low-sugar canned pineapple packed in juice rather than syrup also cuts the overall sugar.

Final Thoughts

Pineapple Upside Down Sugar Cookies are a cheerful, shareable twist on two classics combined into one easy-to-make treat. They’re forgiving, adaptable, and perfect for anyone who loves a little tropical brightness in their baked goods. Try the flavor variations to make them your own, and remember that small adjustments—like drying the pineapple well and monitoring bake times—make a big difference in texture. Whether you bake them for a picnic, a cookie swap, or an everyday indulgence, these cookies are designed to delight every bite.