Short Description

Pineapple Upside-Down Cookies are a creative fusion of a soft, buttery cookie and the iconic pineapple upside-down cake. These treats feature a caramelized fruit topping tucked under a tender cookie base, delivering all the nostalgia of the classic dessert in a handheld form. With every bite, you’ll experience the sunny sweetness of pineapple and cherry, balanced with a soft cookie crumb.

Why You’ll Love This Recipe

Tropical Flavor: The combination of pineapple and maraschino cherry evokes warm, summery vibes in every bite.
Unique Presentation: Mini upside-down cakes in cookie form are both whimsical and visually appealing.
Soft and Chewy Texture: These cookies bake up tender and rich thanks to butter and brown sugar.
Perfect for Parties: Ideal for gatherings, bake sales, or special occasions.
Easy to Make: Uses simple pantry ingredients and basic baking techniques.

Ingredients

(Tip: You can find the complete list of ingredients and their measurements in the recipe card below.)

1 can pineapple slices (drained and patted dry)
1 maraschino cherry per cookie
2½ cups all-purpose flour
1 teaspoon baking powder
¼ teaspoon salt
1 cup granulated sugar
½ cup packed brown sugar
1 large egg
1 teaspoon vanilla extract
1 cup unsalted butter (softened)

Directions

Preheat your oven to 350°F (175°C). Grease the wells of a standard muffin tin.
Place one pineapple ring into each well of the muffin tin. Add a maraschino cherry in the center of each ring.
In a large mixing bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
Beat in the egg and vanilla extract until well combined.
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture, mixing until a soft dough forms.
Scoop dough over the fruit in each muffin well and gently flatten to spread evenly.
Bake for 15–18 minutes, or until the cookie tops are golden brown.
Allow to cool in the tin for a few minutes before carefully flipping each cookie out onto a wire rack to cool completely.

Servings and Timing

Servings: Makes approximately 12–15 cookies
Prep Time: 20 minutes
Bake Time: 15–18 minutes
Total Time: About 35–40 minutes

Variations

Mini Muffin Version: Use mini muffin tins for bite-sized versions of this dessert.
Coconut Twist: Add ¼ cup of shredded coconut to the cookie dough for extra tropical flair.
Spiced Option: Mix in ½ teaspoon of ground cinnamon or nutmeg for a warm flavor note.
Gluten-Free: Substitute all-purpose flour with a 1:1 gluten-free baking flour.
Rum Glaze: Drizzle with a light rum glaze after baking for an adult-friendly twist.

Storage/Reheating

Storage: Store cooled cookies in an airtight container at room temperature for up to 3 days.
Refrigeration: For longer storage, refrigerate for up to 5 days; allow to come to room temperature before serving.
Freezing: Freeze individually wrapped cookies in an airtight container for up to 1 month. Thaw in the refrigerator or at room temperature.
Reheating: Warm in a 300°F (150°C) oven for 5–7 minutes to refresh texture before serving.

FAQs

Can I use fresh pineapple instead of canned?

Yes, you can substitute fresh pineapple slices, but be sure to cut them to fit and pat them dry thoroughly to avoid soggy cookies.

Do I have to use a muffin tin?

Yes, using a muffin tin helps the cookies hold their shape and creates the classic upside-down effect.

Can I make the dough in advance?

Yes, the cookie dough can be made up to 24 hours ahead and stored in the refrigerator. Let it come slightly to room temperature before baking.

How do I prevent the cookies from sticking to the tin?

Make sure to grease the tin well, or use non-stick muffin tins. Running a knife around the edges before flipping can also help.

Can I use margarine instead of butter?

Butter is preferred for flavor and texture, but margarine can be used if necessary.

What’s the best way to flip the cookies?

Let the cookies cool slightly in the tin, then place a wire rack or tray on top and invert the entire muffin tin.

Can I use parchment liners?

No, parchment liners interfere with the caramelized fruit topping. Grease-only tins work best.

What should the texture of the cookies be like?

They should be soft and slightly cakey, resembling the texture of a soft-baked sugar cookie.

Can I make these without the cherry?

Yes, you can omit the cherry or substitute it with another fruit like a blueberry or raspberry.

Pineapple Upside-Down Cookies – A Cookie, A Cake, A Tropical Vacation in Every Bite

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Author: Olivia

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Description

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