Looking for a creative twist on two classic desserts? This recipe for Pineapple Upside Down Sugar Cookies combines the best of both worlds. We start with a simple, from-scratch sugar cookie dough, then top it with the signature elements of the iconic cake: juicy pineapple rings and bright red cherries, all finished with a buttery brown sugar glaze.
These pineapple cookies offer all the delicious, caramelized flavor of the traditional dessert but in a fun, easy-to-make cookie form. Read on to learn how to make these stunning and delicious pineapple upside-down treats that are sure to be a hit.
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pineapple upside down sugar cookies
- Total Time: 30 mins
- Yield: 10–12 servings 1x
- Diet: Vegetarian
Description
Recently, I wanted to capture the magic of a classic dessert in a simpler, more kid-friendly form. That’s when the idea for these incredible pineapple upside down sugar cookies was born!
Ingredients
2 ½ cups All-purpose flour
1 teaspoon Baking soda
½ teaspoon Salt
1 cup Unsalted butter (softened)
¾ cup Granulated sugar
½ cup Brown sugar (packed)
1 Large egg
1 teaspoon Vanilla extract
1 (20 oz) can Canned pineapple rings (in juice, drained well)
10–12 Maraschino cherries (halved)
Instructions
- Drain pineapple rings very well. Pat them dry with paper towels; this prevents soggy cookies. Lightly grease a baking sheet or use parchment paper. Arrange the pineapple slices on the sheet. Place a halved maraschino cherry in the center of each pineapple ring
- In a small bowl, mix the brown sugar. Sprinkle a small amount of brown sugar evenly over each pineapple ring. This creates that iconic sticky topping for your pineapple upside down sugar cookies
- In a large bowl, cream together the softened butter, granulated sugar, and the remaining brown sugar until light and fluffy. A stand mixer works best for these amazing upside down sugar cookies
- Beat in the egg and vanilla extract until fully combined. Scrape down the sides of the bowl to ensure everything mixes properly for our pineapple upside down sugar cookie recipe
- In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Do not overmix the dough for your pineapple sugar cookies
- Scoop about 1-2 tablespoons of cookie dough directly on top of each pineapple slice. Gently flatten the dough slightly, ensuring it covers the pineapple. Bake your pineapple upside down sugar cookies at 375°F (190°C) for 10-12 minutes, or until the edges are lightly golde
- Allow the cookies to cool on the baking sheet for just 5 minutes. This firm ups the caramel. Then, carefully invert each pineapple upside down sugar cookie onto a wire rack. Let them cool completely. Enjoy your delicious pineapple upside down sugar cookies!
Notes
Achieving perfect pineapple upside down sugar cookies requires a few insider tricks. Firstly, always drain your pineapple thoroughly.
Store your leftover pineapple upside down sugar cookies in an airtight container at room temperature for up to 3 days. For longer freshness, place them in the refrigerator for up to a week. You can also freeze these pineapple upside down sugar cookies for up to 2 months. Simply place them in a single layer in an airtight freezer-safe container.
These delightful pineapple upside down sugar cookies are fantastic on their own. However, pairing them with a scoop of vanilla ice cream elevates the experience. A dollop of whipped cream also complements the tangy sweetness beautifully.
Substitutions & Variations: Try other fruits like sliced peaches or apricots. Use a raspberry or a blackberry instead of maraschino cherries. To make gluten-free, swap all-purpose flour for a 1:1 gluten-free baking blend. Add a pinch of cinnamon to the brown sugar. Make mini cookies with smaller pineapple slices.
FAQs: You can use fresh pineapple, but blot it very dry. Sogginess is usually due to too much moisture from pineapple. Dough can be made ahead and refrigerated for up to 2 days; bring to room temperature before baking.
- Prep Time: 20 mins
- Cook Time: 10 mins
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 250 kcal
- Sugar: 20g
- Sodium: 100mg
- Fat: 12g
- Saturated Fat: 7g
- Unsaturated Fat: 5g
- Trans Fat: 0g
- Carbohydrates: 35g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
Keywords: pineapple, upside down, sugar cookies, dessert, kid-friendly, family favorite, classic dessert twist, easy recipe, sweet, tangy, buttery, visually stunning
WHY YOU’LL LOVE THIS RECIPE
- You’ll instantly adore these pineapple upside down sugar cookies. First, they offer a delightful twist on a classic dessert. Furthermore, our pineapple upside down sugar cookie recipe is surprisingly simple to follow.
- Even busy parents can whip up these amazing pineapple upside down sugar cookies with ease. The sweet, tangy pineapple creates a beautiful contrast with the soft, buttery cookie base. It’s a dessert that truly pleases everyone.
- Finally, these pineapple upside down cookies look absolutely stunning on any platter. Impress your guests with these unique upside down sugar cookies. Every bite of these pineapple upside down sugar cookies is pure sunshine!
INGREDIENTS YOU’LL NEED
| Ingredient | Quantity |
|---|---|
| All-purpose flour | 2 ½ cups |
| Baking soda | 1 teaspoon |
| Salt | ½ teaspoon |
| Unsalted butter (softened) | 1 cup (2 sticks) |
| Granulated sugar | ¾ cup |
| Brown sugar (packed) | ½ cup |
| Large egg | 1 |
| Vanilla extract | 1 teaspoon |
| Canned pineapple rings (in juice, drained well) | 1 (20 oz) can |
| Maraschino cherries (halved) | 10-12 |
SUBSTITUTIONS & VARIATIONS
You can certainly get creative with your pineapple upside down sugar cookies! For instance, try other fruits. Sliced peaches or apricots can make delicious upside down sugar cookies.
Instead of maraschino cherries, use a raspberry or a blackberry for a different pop of color. To make these pineapple upside down sugar cookies gluten-free, simply swap out the all-purpose flour for a 1:1 gluten-free baking blend. Consider adding a pinch of cinnamon to the brown sugar for an extra warm spice note in your pineapple upside down cookies.
You can even make mini pineapple upside down sugar cookies using smaller pineapple slices. These delightful cookies are very versatile!
You can certainly get creative with your pineapple upside down sugar cookies, experimenting with various fruits and even making them gluten-free. If you enjoy baking with fruit and oats for a wholesome and versatile treat, don’t miss out on making Banana Oatmeal Bars for your family.
STEP-BY-STEP INSTRUCTIONS
Making these pineapple upside down sugar cookies is straightforward. Follow these steps for perfect results every time.
- Prepare Pineapple & Pan: First, drain pineapple rings very well. Pat them dry with paper towels; this prevents soggy cookies. Lightly grease a baking sheet or use parchment paper. Arrange the pineapple slices on the sheet. Place a halved maraschino cherry in the center of each pineapple ring.
- Make Caramel Topping: Next, in a small bowl, mix the brown sugar. Sprinkle a small amount of brown sugar evenly over each pineapple ring. This creates that iconic sticky topping for your pineapple upside down sugar cookies.
- Cream Butter & Sugars: Now, in a large bowl, cream together the softened butter, granulated sugar, and the remaining brown sugar until light and fluffy. A stand mixer works best for these amazing upside down sugar cookies.
- Add Egg & Vanilla: Then, beat in the egg and vanilla extract until fully combined. Scrape down the sides of the bowl to ensure everything mixes properly for our pineapple upside down sugar cookie recipe.
- Combine Dry Ingredients: In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Do not overmix the dough for your pineapple sugar cookies.
- Scoop & Bake: Finally, scoop about 1-2 tablespoons of cookie dough directly on top of each pineapple slice. Gently flatten the dough slightly, ensuring it covers the pineapple. Bake your pineapple upside down sugar cookies at 375°F (190°C) for 10-12 minutes, or until the edges are lightly golden.
- Cool & Flip: Allow the cookies to cool on the baking sheet for just 5 minutes. This firm ups the caramel. Then, carefully invert each pineapple upside down sugar cookie onto a wire rack. Let them cool completely. Enjoy your delicious pineapple upside down sugar cookies!
PRO TIPS FOR SUCCESS
Achieving the perfect texture and moisture balance is crucial for these delightful pineapple upside down sugar cookies, much like it is for many classic baked goods. For another dessert that truly benefits from careful preparation to achieve its signature rich and moist consistency, explore our recipe for an Easy Traditional Fruitcake: The Heartwarming Holiday Classic, Redeemed.
STORAGE & REHEATING TIPS
Store your leftover pineapple upside down sugar cookies in an airtight container at room temperature for up to 3 days. For longer freshness, place them in the refrigerator for up to a week. You can also freeze these pineapple upside down sugar cookies for up to 2 months.
Simply place them in a single layer in an airtight freezer-safe container. Thaw frozen pineapple upside down sugar cookies at room temperature before enjoying them. A quick zap in the microwave can warm them slightly, enhancing their deliciousness.
WHAT TO SERVE WITH THIS RECIPE
These delightful pineapple upside-down sugar cookies are fantastic on their own, but pairing them with other desserts or toppings truly elevates the experience. If you’re looking for another stunning and versatile dessert perfect for serving with fruit or cream, consider trying the best Berry Trifle Cake You’ll Ever Make.
FAQs
Can I use fresh pineapple for these pineapple upside down sugar cookies?
Absolutely! If using fresh pineapple, slice it thinly and make sure to blot it very dry. Fresh pineapple can be juicier, so extra drying is key for these pineapple upside down sugar cookies.
Why are my pineapple upside down sugar cookies soggy?
Sogginess usually comes from too much moisture. Ensure you drain and thoroughly pat dry your pineapple rings before placing them on the baking sheet. This is crucial for excellent pineapple upside down sugar cookies.
Can I make the dough for these pineapple upside down sugar cookies ahead of time?
Yes, you can! Prepare the cookie dough as instructed, wrap it tightly in plastic, and refrigerate it for up to 2 days. Let it come to room temperature slightly before scooping onto the pineapple slices to bake your pineapple upside down sugar cookies.
The concept of an ‘upside-down’ dessert, where fruit is placed at the bottom of a pan and inverted after baking, ensures beautiful caramelization and a striking presentation. This method is famously utilized in dishes like the classic pineapple upside-down cake, inspiring many variations, including these charming sugar cookies.
NUTRITION INFORMATION (PER SERVING)
These pineapple upside down sugar cookies are a delightful treat. Here is an estimated nutritional breakdown per cookie.
| Nutrient | Amount |
|---|---|
| Calories | 250 kcal |
| Total Fat | 12g |
| Saturated Fat | 7g |
| Cholesterol | 30mg |
| Sodium | 100mg |
| Total Carbohydrates | 35g |
| Dietary Fiber | 1g |
| Total Sugars | 20g |
| Protein | 2g |