Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies offer a delicious twist on the classic cake. Soft sugar cookies form the base, topped with caramelized pineapple slices and maraschino cherries, all drizzled with a brown sugar-butter mixture that creates a gorgeous glaze when baked. The cookie dough is made by creaming together softened butter and granulated sugar, then blending in an egg and vanilla extract. A mix of all-purpose flour, salt, and baking soda is incorporated to form a soft dough. This easy yet impressive dessert is baked in a muffin tin, allowing each cookie to hold its caramelized fruit topping beautifully. The result is a tender, flavorful cookie that’s perfect for celebrations, afternoon snacks, or simply for satisfying your sweet tooth.

Clare Greco
Updated on Monday 02 December 2024
Pineapple Upside Down Sugar Cookies
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Pineapple Upside Down Sugar Cookies are a delightful take on a classic dessert. With the soft, buttery texture of sugar cookies and the sweet-tart flavors of caramelized pineapple and cherries, they bring the best of both worlds to your dessert table. The cookies start with a rich base of creamed butter and sugar, enhanced by a hint of vanilla and an egg for a perfectly moist dough. Flour, baking soda, and salt add structure and balance, while the topping is a simple but delicious blend of melted butter and brown sugar, creating a caramel-like glaze for the fruit.

INGREDIENTS

  • Unsalted butter (melted): 1/4 cup for the caramelized topping
  • Brown sugar: 1/3 cup for topping
  • Pineapple slices: 12, from canned
  • Maraschino cherries: 12
  • Granulated sugar: 1 cup
  • Unsalted butter (softened): 1/2 cup for cookie dough
  • Large egg: 1
  • Vanilla extract: 1 tsp
  • All-purpose flour: 1 1/2 cups
  • Salt: 1/4 tsp
  • Baking soda: 1/4 tsp

INSTRUCTIONS

Step 1:
Preheat oven to 350°F. Mix melted butter and brown sugar together. Place a teaspoon of the mixture into each muffin tin compartment, then add a pineapple slice and a maraschino cherry on top.
Step 2:
In a large bowl, cream together granulated sugar and softened butter until light and fluffy. Beat in the egg and vanilla extract.
Step 3:
In a separate bowl, whisk together flour, salt, and baking soda. Gradually add the dry ingredients to the wet mixture until fully combined.
Step 4:
Form dough balls and flatten slightly. Place each on top of the pineapple and cherry in the muffin tin compartments.
Step 5:
Bake for 14-16 minutes, or until the cookies are golden brown.
Step 6:
Let cookies cool in the muffin tin for 5 minutes, then gently remove.

Serving and Storage Tips

  • Serve warm for the best caramelized flavor.
  • Store in an airtight container for up to 3 days at room temperature or refrigerate for a week.

Helpful Notes

  • For a more intense flavor, use fresh pineapple instead of canned.
  • Ensure the butter and sugar mixture is evenly distributed to prevent sticking.

Tips from Well-Known Chefs

  • Chef Clara recommends using silicone muffin tins for easier removal of the cookies.
  • Add a dash of cinnamon to the topping for a warm spice note.

Classic Dessert with a Twist

These cookies put a fun spin on traditional pineapple upside-down cake, offering a bite-sized treat that’s easy to make and serve.

Rich, Sweet, and Perfectly Balanced

The caramelized brown sugar, tart pineapple, and buttery sugar cookie combine for an irresistible flavor profile that will have guests asking for more.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used, but make sure to cut it into thin slices.

Do I need to grease the muffin tin?

It’s recommended to lightly grease the muffin tin to prevent sticking.

Can I substitute the maraschino cherries?

Yes, you can use fresh cherries or even omit them if preferred.

How do I store leftovers?

Store in an airtight container at room temperature for up to 3 days or refrigerate for up to a week.

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Some more ideas

Pineapple Upside Down Sugar Cookies combine the soft, buttery texture of sugar cookies with a sweet and tangy topping of caramelized pineapple slices and cherries. The cookies are baked upside down in muffin tins, ensuring that every bite is filled with fruity goodness and rich, caramelized brown sugar. Easy to make and visually impressive, these cookies are perfect for parties, family gatherings, or whenever you want to surprise your guests with a unique treat. With just the right amount of sweetness and a beautiful presentation, these cookies bring a taste of summer to any table.

Pineapple Sugar Cookies

Soft sugar cookies topped with caramelized pineapple and cherries, drizzled with a brown sugar glaze for a delicious twist.

Prep Time
15 Minutes
Cook Time
15 Minutes
Total Time
30 Minutes

Category: Sweet Treats

Difficulty: Intermediate

Cuisine: Dessert

Yield: 12 Servings (12 cookies)

Dietary: Vegetarian

Ingredients

01 1/4 cup unsalted butter, melted.
02 1/3 cup brown sugar.
03 12 pineapple slices (from canned).
04 12 maraschino cherries.
05 1 cup granulated sugar.
06 1/2 cup unsalted butter, softened.
07 1 large egg.
08 1 tsp vanilla extract.
09 1 1/2 cups all-purpose flour.
10 1/4 tsp salt.
11 1/4 tsp baking soda.

Instructions

Step 01

Preheat oven to 350°F. Mix melted butter and brown sugar together. Place a teaspoon of the mixture into each muffin tin compartment, then add a pineapple slice and a maraschino cherry on top.

Step 02

In a large bowl, cream together granulated sugar and softened butter until light and fluffy. Beat in the egg and vanilla extract.

Step 03

In a separate bowl, whisk together flour, salt, and baking soda. Gradually add the dry ingredients to the wet mixture until fully combined.

Step 04

Form dough balls and flatten slightly. Place each on top of the pineapple and cherry in the muffin tin compartments.

Step 05

Bake for 14-16 minutes, or until the cookies are golden brown.

Step 06

Let cookies cool in the muffin tin for 5 minutes, then gently remove.

Notes

  1. These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside-down cake with a soft sugar cookie base. The caramelized pineapple and cherries on top make for a delightful presentation and a burst of sweet flavor.

Nutrition Facts (Per Serving)

It is important to consider this information as approximate and not to use it as definitive health advice.
  • Calories: ~
  • Total Fat: ~
  • Total Carbohydrate: ~
  • Protein: ~