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Pineapple Upside-Down Cookies

Introduction

I still remember the first time I tasted Pineapple Upside-Down Cookies. I was just a kid, standing on a stool in my grandma’s cozy kitchen, helping her place cherries in the middle of golden pineapple rings.

That warm, caramel aroma filling the air made it feel like magic. Years later, I craved that nostalgic flavorβ€”but in a handheld treat. I gave it a try… and to my surprise, Pineapple Upside-Down Cookies turned out even better than I imagined. Now, it’s your turn to fall in love with them.

Explore all our sweet creations in the Cookies & Bars collection.

The Charm of Pineapple Upside-Down Cookies

Pineapple Upside-Down Cookies are inspired by the classic cake that became a household favorite in the early 20th century. Traditionally baked in cast-iron skillets, the cake’s signature caramelized topping and sweet-tart fruit flavor made it a dessert-table staple. As baking evolved, so did the recipeβ€”giving rise to the delightful bite-sized version we enjoy today.

What makes Pineapple Upside-Down Cookies so appealing now is the blend of retro charm and modern convenience. They’re easy to serve, easy to store, and irresistibly photogenicβ€”perfect for today’s social media generation and nostalgic food lovers alike.

These Pineapple Upside-Down Cookies bring together the caramelized sweetness of cake in a chewy, handheld cookie form.

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Stack of pineapple upside-down cookies topped with cherries and sugar crystals on a ceramic plate with crumbs

Pineapple Upside-Down Cookies

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These Pineapple Upside-Down Cookies combine the golden caramel flavor of the retro cake with the ease of a handheld cookie. Each bite features a glossy pineapple ring, a sweet cherry center, and a soft, buttery cookie base that melts in your mouth. Perfect for holidays, potlucks, or whenever nostalgia strikes.Ready to bake a crowd-pleasing classic? Try this modern twist on a vintage favorite today!

  • Total Time: 40 minutes
  • Yield: 12 cookies

Ingredients

Scale

Topping Layer:

  • 1/2 cup 1 stick unsalted butter, melted
  • 1/2 cup light brown sugar
  • 6 canned pineapple rings (halved or trimmed to fit molds)
  • 6 maraschino cherries

Cookie Dough:

  • 1 cup 2 sticks unsalted butter, room temperature
  • 1 cup granulated sugar
  • 1/2 cup packed light brown sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/4 tsp salt
  • 2 tsp cornstarch

Instructions

Step 1: Prepare the Topping

  1. Preheat oven to 350Β°F (175Β°C).
  2. Lightly grease or spray a muffin pan.
  3. Pour 1 tsp melted butter and 1 tsp brown sugar into each muffin cup.
  4. Place a halved pineapple ring and one cherry in the center of each.

Step 2: Make the Cookie Dough

  1. In a large bowl, beat softened butter with granulated and brown sugars until fluffy.
  2. Add eggs one at a time, then mix in vanilla and sour cream.
  3. In another bowl, whisk flour, baking powder, baking soda, salt, and cornstarch.
  4. Gradually incorporate the dry mixture into the wet mixture to form a soft dough.

Step 3: Assemble and Bake

  1. Spoon or scoop the cookie dough over the pineapple in each cup, filling almost to the top.
  2. Bake for 18–22 minutes, or until golden and set.
  3. Let cool for 10 minutes, then carefully invert cookies onto a wire rack.

Notes

🧾 Nutrition Information (per cookie)

  • Calories: 190 kcal

  • Fat: 9 g

  • Saturated Fat: 5.5 g

  • Carbohydrates: 26 g

  • Sugar: 16 g

  • Protein: 2 g

  • Fiber: 0.5 g

  • Sodium: 75 mg

  • Prep Time: 20 minutes
  • Cook Time: 20 minutes
  • Category: Cookies, Dessert
  • Cuisine: American

Satisfy your fruit-filled cravings with these Tasty Peach Cobbler Cookies.

Ingredients That Make the Magic Happen

The ingredients may be simple, but every component plays a key role in the cookie’s flavor and texture:

  • Butter: Adds richness and creates that irresistible caramel layer.
  • Brown Sugar: Essential for that deep, molasses-sweet base.
  • Pineapple Rings: Choose canned or freshβ€”both work beautifully when sliced to fit.
  • Maraschino Cherries: A pop of color and sweetness.
  • Vanilla & Sour Cream: Enhance the dough’s flavor and moisture.

Tips for Ingredient Quality:

  • Use unsalted, high-fat butter for better control over saltiness and richer flavor.
  • Opt for organic cherries if possibleβ€”they bring better color and cleaner taste.
  • Drain pineapple slices well to prevent soggy bottoms.

Step-by-Step Pineapple Upside-Down Cookie Recipe

Six pineapple upside-down cookies with cherries placed on white marble surface next to gold fork and white napkin

Prepare the Caramelized Topping

  1. Preheat oven to 350Β°F (175Β°C). Lightly grease a muffin or cookie pan.
  2. In each mold, spoon a teaspoon of melted butter and sprinkle with brown sugar.
  3. Add a slice of pineapple and place a cherry in the center.

Make the Cookie Dough

  1. In a bowl, cream butter and granulated sugar until fluffy.
  2. Add eggs, vanilla extract, and sour cream. Mix until smooth.
  3. In a separate bowl, whisk flour, baking powder, salt, and cornstarch.
  4. Combine the dry and wet ingredients into a soft dough.

Assemble and Bake

  1. Scoop the dough onto the prepared fruit-topped molds.
  2. Bake for 18–22 minutes or until golden brown and set.
  3. Cool for 10 minutes, then carefully invert onto a wire rack.

You can even gift Pineapple Upside-Down Cookies in decorative boxesβ€”they look as good as they taste.

Add a refreshing twist to your treats with Raspberry Lemonade Cookies.

Pro Tips for Baking the Perfect Batch

Pineapple Upside-Down Cookies
  • Prevent sticking: Use non-stick spray or silicone molds for easy release.
  • Invert while warm: Letting the cookies sit too long in the pan can make them stick.
  • Store in layers with parchment paper between to keep them intact.

Health and Nutrition Aspects

While Pineapple Upside-Down Cookies are indulgent, they can be adjusted to meet dietary goals. On average, one cookie contains around 170–200 calories depending on size.

For a healthier version:

  • Substitute some of the sugar with applesauce or monk fruit sweetener.
  • Use gluten-free flour blends and dairy-free sour cream for special diets.

Pineapples themselves are rich in vitamin C and antioxidants, while butter provides essential fatty acids and fat-soluble vitamins.

Pineapple Upside-Down Cookies are not just cuteβ€”they’re packed with nostalgic flavor in every bite.

Creative Twists on the Classic Cookie

  • Mini Cupcake Style: Use mini muffin tins for adorable bite-sized treats.
  • Flavor Boosts: Add shredded coconut, chopped pecans, or a splash of dark rum to the batter.
  • Chocolate Drizzle: Melt a bit of dark chocolate and drizzle over cooled cookies for a fusion twist.

Serving Ideas and Pairings

Pineapple Upside-Down Cookies are perfect for:

  • Potlucks and BBQs: Easy to serve without slicing.
  • Holidays: A great tropical twist during colder months.
  • Kids’ Parties: The bright colors make them a hit with little ones.

Pair them with:

  • Iced herbal tea or coconut milk for a tropical feel.
  • A scoop of vanilla bean ice cream for dessert.

Common Mistakes to Avoid

  • Overbaking dries out the doughβ€”remove when lightly golden.
  • Using too much juice from the pineapple can make the topping mushy.
  • Letting them cool too long in the pan can lead to sticking or breaking.

If a cookie sticks, gently warm the pan again in the oven for a minute before trying to release.

Indulge in the gooey delight of our signature Best S’mores Cookies.

Storage, Freezing, and Reheating Tips

  • Room Temperature: Store in an airtight container for up to 3 days.
  • Freezer-Friendly: Flash freeze on a tray, then transfer to a zip-top bag. They keep well for 1–2 months.
  • Reheat: Warm in the oven at 300Β°F for 5–7 minutes for that fresh-baked texture.

Frequently Asked Questions

Does pineapple upside-down cake get soggy?

Yes, if left uncovered or stored improperly. Always cool completely and store in a dry container.

How long can you keep pineapple upside-down cake?

Usually 3 days at room temperature or up to 5 days in the fridge, tightly covered.

How to know when a pineapple upside-down cake is done?

Insert a toothpick in the center; it should come out clean. The top should be golden and firm.

What does pineapple upside down taste like?

It’s a combination of tangy, sweet, buttery caramel and soft vanilla cake or cookie baseβ€”comforting and fruity.

Let these Pineapple Upside-Down Cookies bring joy to your kitchen like they did in mine. Bake them once, and they’ll be a go-to treat you’ll never forget.

Brighten your bake with the tangy-sweet flavor of Lemon Raspberry Cookies.

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