Name: Pineapple Upside Down Sugar Cookies
Prep time: 15 min
Cook time: 12 min
Total time: 27 min
Cuisine: American
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

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Pineapple Upside Down Sugar Cookies are a sunny, nostalgic twist on two classic favorites — the caramelized pineapple of an upside-down cake and the soft, buttery snap of a sugar cookie.

For a fun little twist on presentation and flavor, you can also compare texture and serving ideas with similar treats like mini pineapple upside-down cheesecakes, which show how pineapple and caramelized sugar pair beautifully in small, shareable desserts.

Why make this Pineapple Upside Down Sugar Cookies recipe

These Pineapple Upside Down Sugar Cookies are worth making because they capture the best parts of a retro dessert in bite-sized, portable form. The cookies give you the buttery, tender crumb of a sugar cookie, while a caramelized pineapple ring or chunk on top adds brightness and a touch of tropical sweetness. They’re approachable for home bakers, fun for parties, and flexible enough for summer barbecues or cozy winter gatherings.

This recipe is also a great way to use canned pineapple when fresh isn’t in season. The method is straightforward, requiring common pantry ingredients and minimal tools, yet the result feels special. If you love the nostalgic look of pineapple rings and cherries on a cake but want something easier to pass around, these cookies deliver.

How to make Pineapple Upside Down Sugar Cookies

These cookies combine a classic sugar-cookie dough with the caramel-like topping that makes upside-down desserts so irresistible. You’ll cream butter and sugar, add an egg and vanilla, then fold in flour and baking soda. After shaping the dough and topping each cookie with a well-drained pineapple ring or a pineapple chunk, a light sprinkle of sugar helps the fruit caramelize in the oven.

Start by chilling the dough briefly if it becomes too soft, and use a cookie scoop for even portions. Bake until the cookie edges are set and the pineapple looks glossy. Let the cookies cool on the tray for a few minutes to set the topping, then transfer them to a rack.

Ingredients

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 substitutions:

Unsalted butter: Using unsalted butter lets you control the salt level. If you only have salted butter, omit or reduce the added salt. For a dairy-free option, use a plant-based butter substitute and expect a slightly different texture.
Granulated sugar: You can substitute half the white sugar with light brown sugar for a more caramel note, but that will change the texture slightly (a touch chewier).
Vanilla extract: Optional but recommended for depth; you can substitute with a light citrus zest (lemon or orange) for a brighter flavor.
Flour: All-purpose flour can be swapped 1:1 with a gluten-free blend designed to replace AP flour. If you use a gluten-free flour that lacks xanthan gum, check the package directions—some blends need binders added.
Baking soda: Don’t skip the leavener — it helps the cookies spread and lift properly.
Canned pineapple rings: Well-drained rings are essential to prevent soggy cookies. If you prefer fresh pineapple, slice thinly and pat dry; fresh fruit will have a brighter but less syrupy note.
Additional sugar for sprinkling: This encourages caramelization on the pineapple. You can use turbinado sugar for a crunchier, darker crust.

Directions

Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper or a silicone mat.
Drain the canned pineapple well, laying the rings on paper towels and patting the tops dry. If you prefer smaller cookies, cut rings into halves or quarters; whole rings work best on larger cookies.
In a large bowl, cream 1 cup softened unsalted butter with 1 cup granulated sugar until light and fluffy, about 2–3 minutes with an electric mixer.
Beat in 1 large egg and 1 teaspoon vanilla extract (if using) until combined and smooth.
In a separate bowl, whisk together 2 cups all-purpose flour, 1 teaspoon baking soda, and 1/2 teaspoon salt.
Gradually add the dry ingredients to the wet mixture, mixing just until incorporated. Don’t overmix — you want a tender cookie.
Use a cookie scoop or tablespoon to portion dough onto the prepared baking sheets, spacing cookies about 2 inches apart. For larger cookies that fit a whole pineapple ring, use roughly 2 tablespoons of dough per cookie and flatten slightly.
Gently press a pineapple ring (or a piece of ring) into the center of each dough mound. If the pineapple piece is thicker than the dough mound, press carefully so the fruit is slightly embedded but the dough still surrounds it.
Lightly sprinkle about 1/4 teaspoon of the additional sugar over each pineapple topping for caramelization.
Bake in the preheated oven for 10–14 minutes for smaller cookies or 14–18 minutes for larger cookies, until the cookie edges are set and the pineapple begins to brown lightly around the edges.
Remove cookies from the oven and let them cool on the baking sheet for 5 minutes so the topping can set, then transfer to a wire rack to cool completely.

Pro Tips for Success Pineapple Upside Down Sugar Cookies

Chill slightly if dough softens: If your dough becomes too soft to shape, chill it for 15–20 minutes. Cold dough holds pineapple toppings better and prevents excessive spreading.
Dry pineapple thoroughly: Excess moisture is the most common cause of soggy cookies. Lay pineapple rings on paper towels and blot them well before placing them on dough.
Use a cookie scoop for uniformity: Evenly sized cookies bake more predictably. If you’re fitting whole pineapple rings, use slightly larger scoops and flatten gently.
Watch the edges, not the center: Sugar cookies can look underdone in the center but be set at the edges. Remove cookies when edges are firm and centers are just set — they’ll continue to cook slightly as they cool.
Toast sugar for deeper color: For extra caramel notes, lightly toast the sprinkle sugar in a skillet before adding to the pineapple (careful not to burn it), or swap with turbinado sugar.
Avoid overcrowding the sheet: Give cookies enough space to spread. Crowding can cause odd shapes and uneven caramelization.

Flavor Variations Pineapple Upside Down Sugar Cookies

Cherry-on-top classic: After baking and while the pineapple is still tacky, add a maraschino cherry or a quartered glace cherry to the center for a classic pineapple-upside-down look.
Coconut-lime twist: Add 1/2 cup sweetened shredded coconut to the dough and 1 teaspoon lime zest to the wet ingredients. Coconut pairs beautifully with pineapple for a tropical cookie.
Spiced caramel: Swap 1/4 cup of the granulated sugar for brown sugar, and add 1/2 teaspoon ground cinnamon and a pinch of nutmeg to the dry ingredients for warm, cozy notes.
Rum-less glazed: For a more grown-up flavor without alcohol, brush a thin mix of pineapple juice and a splash of lemon juice over the pineapple immediately after baking for a glossy, tangy finish.
Mini tart version: Press dough into mini muffin tin cups, add a small pineapple chunk, and bake for mini tartlets — a portable, bite-sized option.

Serving Suggestions Pineapple Upside Down Sugar Cookies

Serve these cookies warm or at room temperature. They’re delicious on their own, but a few simple pairings elevate them:

Afternoon tea or coffee: Let the cookie’s buttery softness pair with a robust coffee or black tea.
With vanilla whipped cream: A dollop of lightly sweetened whipped cream adds a creamy counterpoint that’s lovely with the caramelized fruit.
Ice cream sandwich: Place a scoop of vanilla or coconut ice cream between two cooled cookies for a tropical ice cream sandwich.
Party platter: Arrange cookies on a platter with fresh pineapple slices, toasted coconut, and cherries for a bright, shareable dessert board.
Brunch accent: These cookies add sweet flair to a brunch spread — they’re a fun companion to pancakes, yogurt, and fresh fruit.

Storage and Freezing Instructions Pineapple Upside Down Sugar Cookies

Short-term storage:

Room temperature: Store cooled cookies in an airtight container at room temperature for up to 3 days. Use parchment paper between layers to prevent sticking.
Refrigerator: If your climate is humid or the pineapple topping makes cookies moist, store them in the refrigerator in an airtight container for up to 5 days. Bring them back to room temperature before serving.

Freezing:

Freeze unbaked dough: Portion the cookie dough and freeze scooped dough balls on a lined tray until firm, then transfer to a zip-top bag for up to 3 months. When ready to bake, thaw in the fridge for a few hours, press pineapple topping on, and bake as directed (you may need an extra minute or two).
Freeze baked cookies: Place cooled baked cookies on a tray and freeze until firm, then transfer to an airtight container or freezer bag for up to 2 months. Thaw overnight in the refrigerator or at room temperature.
Prevent sogginess: To maintain texture, wrap cookies individually in plastic wrap before placing in a container, especially if freezing. Re-crisp in a 300°F oven for 5–7 minutes if needed after thawing.

Nutrition Facts (Per Serving)

Nutrition Facts (Per Serving) — calories: approximately 151 kcal, protein: 1.4 g, carbs: 18.3 g, fat: 8.0 g, fiber: 0.4 g, sodium: 104 mg.

Notes on nutrition:

These values are estimates based on the full recipe yielding about 24 cookies and standard ingredient nutrition data. Actual values will vary by brand and exact portion size.
To lower calories, make smaller cookies or reduce the butter slightly (note: texture will change).
For higher protein, serve with Greek yogurt or a small glass of milk.

FAQ About Pineapple Upside Down Sugar Cookies

What makes these cookies “upside down” compared to regular sugar cookies?

"Pineapple upside-down" refers to the topping placement: instead of frosting or sprinkles on top, a caramelized pineapple piece sits on the cookie surface, mimicking the classic upside-down cake where fruit spells out the top when inverted. In these cookies, the pineapple is added before baking and caramelizes with a sprinkle of sugar. The result is a glossy fruity topping that sits on the cookie, similar to the cake’s fruit layer but in single-serve form.

Can I use fresh pineapple instead of canned pineapple rings?

Yes, you can use fresh pineapple. Choose ripe but firm fruit, slice thinly so it’s not overly juicy, and pat each slice dry on paper towels. Fresh pineapple gives a brighter, less syrupy flavor but can release more moisture, so drying and possibly searing briefly in a hot skillet can help concentrate sugars and reduce sogginess.

How do I prevent the pineapple from making the cookies soggy?

The key is proper draining and drying. Lay canned rings on paper towels and press gently to remove surface syrup. If fruit is very wet, dab each piece again just before topping the dough. Chilling the dough slightly also helps it better support the fruit. Optionally, sprinkle a touch of flour under the pineapple (on the dough) to create a moisture barrier, or lightly caramelize the fruit in a skillet to evaporate excess moisture first.

Are these cookies suitable for gluten-free diets?

They can be made gluten-free by using a 1:1 gluten-free all-purpose flour blend that contains a binder like xanthan gum. Some gluten-free flours absorb liquids differently, so you may need to rest the dough briefly to hydrate the flour, and the texture may be slightly crumblier. Follow the same proportions and watch baking time; gluten-free cookies sometimes brown faster.

What’s the best way to reheat cookies with pineapple topping?

For a warm, fresh-from-the-oven feel, heat cookies on a baking sheet at 300°F (150°C) for 5–7 minutes; this helps the pineapple glaze regain gloss and warms the center without over-browning. Microwaving can soften cookies too much or make them soggy, so the oven is preferred.

Can I make these cookies ahead for a party?

Yes. Store baked cookies in an airtight container at room temperature up to three days or in the refrigerator up to five days. For longer ahead-of-time prep, freeze baked cookies in a single layer until firm, then transfer to a container; thaw before serving and reheat briefly if you want them warm. If preparing dough ahead, freeze scooped dough balls and bake on the event day for the freshest cookies.

Final Thoughts

Pineapple Upside Down Sugar Cookies are a cheerful, nostalgic treat that’s easy enough for weekday baking yet special enough for gatherings. They marry familiar sugar-cookie comfort with the sweet-tart brightness of pineapple, and the simple sprinkle of sugar creates a tiny caramelized crown that makes each bite sing. Whether you keep them classic with rings and cherries or experiment with coconut, lime, or toasted sugars, these cookies are versatile, crowd-pleasing, and sure to become a favorite in your recipe rotation. Enjoy baking, sharing, and savoring each delightful bite.

Pineapple Upside Down Sugar Cookies That Delight Every Bite