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 grandmaβs 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 flavorβbut in a handheld treat. I gave it a tryβ¦ and to my surprise, Pineapple Upside-Down Cookies turned out even better than I imagined. Now, itβs 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 cakeβs signature caramelized topping and sweet-tart fruit flavor made it a dessert-table staple. As baking evolved, so did the recipeβgiving 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. Theyβre easy to serve, easy to store, and irresistibly photogenicβperfect for todayβs 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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Pineapple Upside-Down Cookies
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
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
- Preheat oven to 350Β°F (175Β°C).
- Lightly grease or spray a muffin pan.
- Pour 1 tsp melted butter and 1 tsp brown sugar into each muffin cup.
- Place a halved pineapple ring and one cherry in the center of each.
Step 2: Make the Cookie Dough
- In a large bowl, beat softened butter with granulated and brown sugars until fluffy.
- Add eggs one at a time, then mix in vanilla and sour cream.
- In another bowl, whisk flour, baking powder, baking soda, salt, and cornstarch.
- Gradually incorporate the dry mixture into the wet mixture to form a soft dough.
Step 3: Assemble and Bake
- Spoon or scoop the cookie dough over the pineapple in each cup, filling almost to the top.
- Bake for 18β22 minutes, or until golden and set.
- Let cool for 10 minutes, then carefully invert cookies onto a wire rack.
Notes
π§Ύ 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 cookieβs 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 freshβboth work beautifully when sliced to fit.
- Maraschino Cherries: A pop of color and sweetness.
- Vanilla & Sour Cream: Enhance the doughβs 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 possibleβthey bring better color and cleaner taste.
- Drain pineapple slices well to prevent soggy bottoms.
Step-by-Step Pineapple Upside-Down Cookie Recipe

Prepare the Caramelized Topping
- Preheat oven to 350Β°F (175Β°C). Lightly grease a muffin or cookie pan.
- In each mold, spoon a teaspoon of melted butter and sprinkle with brown sugar.
- Add a slice of pineapple and place a cherry in the center.
Make the Cookie Dough
- In a bowl, cream butter and granulated sugar until fluffy.
- Add eggs, vanilla extract, and sour cream. Mix until smooth.
- In a separate bowl, whisk flour, baking powder, salt, and cornstarch.
- Combine the dry and wet ingredients into a soft dough.
Assemble and Bake
- Scoop the dough onto the prepared fruit-topped molds.
- Bake for 18β22 minutes or until golden brown and set.
- Cool for 10 minutes, then carefully invert onto a wire rack.
You can even gift Pineapple Upside-Down Cookies in decorative boxesβthey look as good as they taste.
Add a refreshing twist to your treats with Raspberry Lemonade Cookies.
Pro Tips for Baking the Perfect Batch

- 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 170β200 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 cuteβtheyβre 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.
- Kidsβ 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 doughβremove 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 Sβmores 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 1β2 months.
- Reheat: Warm in the oven at 300Β°F for 5β7 minutes for that fresh-baked texture.
Frequently Asked Questions
Does pineapple upside-down cake get soggy?
How long can you keep pineapple upside-down cake?
How to know when a pineapple upside-down cake is done?
What does pineapple upside down taste like?
Let these Pineapple Upside-Down Cookies bring joy to your kitchen like they did in mine. Bake them once, and theyβll be a go-to treat youβll never forget.
Brighten your bake with the tangy-sweet flavor of Lemon Raspberry Cookies.