Pineapple Upside Down Sugar Cookies: A Chewy, Tropical Twist.

The classic pineapple upside-down cake is a staple of retro baking, beloved for its caramelized fruit and moist crumb.¹However, transforming those same flavors into a portable, chewy sugar cookie creates a completely different experience. These cookies take the buttery, vanilla-heavy base of a classic sugar cookie and top it with a ring of caramelized pineapple and a bright cherry center.²+1

I developed this recipe because I wanted the iconic “upside-down” look without the commitment of a full cake. By macerating the pineapple rings in brown sugar before baking, you create a natural glaze that seeps into the cookie dough, resulting in a golden, jammy edge and a soft, tender middle. It is a reliable, visually charming recipe that brings a bit of tropical sunshine to any cookie platter.

Ingredients

The Cookie Base

• 1 Cup Unsalted Butter: Softened to room temperature.
• 1 Cup Granulated Sugar.
• 1 Large Egg: Room temperature.
• 1 Teaspoon Pure Vanilla Extract.
• 1/2 Teaspoon Almond Extract: This provides that nostalgic “cake” flavor.
• 2.5 Cups All-Purpose Flour.
• 1/2 Teaspoon Baking Soda.
• 1/4 Teaspoon Sea Salt.

The Tropical Topping

• 20–24 Pineapple Tidbits: Canned or fresh (if using canned, drain and pat very dry).
• 12 Maraschino Cherries: Halved.
• 1/4 Cup Brown Sugar: For dipping the pineapple.
• 2 Tablespoons Melted Butter: To brush over the fruit.

Instructions

1. Prep the Fruit

The biggest challenge with this recipe is moisture. If the pineapple is too wet, the cookies will spread and become soggy. Take your pineapple tidbits and place them between several layers of paper towels, pressing down firmly to remove excess juice. Dip each piece of pineapple into the brown sugar so one side is well-coated.

2. Cream the Butter and Sugar

In a large bowl, cream together the softened butter and granulated sugar until the mixture is pale and fluffy (about 2–3 minutes). Add the egg, vanilla extract, and almond extract, beating until fully incorporated.

3. Mix the Dry Ingredients

In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Do not over-mix, or the cookies will lose their tender, chewy texture.

4. Shape the Cookies

Scoop about two tablespoons of dough at a time and roll them into balls. Place them on a parchment-lined baking sheet, leaving about 2 inches of space between each. Use the bottom of a glass to gently flatten the balls into thick discs.

5. Assemble the “Upside Down” Look

Press three or four pineapple tidbits (sugar-side up) into the top of each cookie in a circular pattern. Place half a maraschino cherry in the very center. Lightly brush the fruit with a tiny bit of melted butter to help the caramelization process.

6. Bake and Cool

Bake at 350°F (175°C) for 12 to 14 minutes. The edges should be just starting to turn golden brown, but the centers should still look slightly soft. Let the cookies cool on the baking sheet for at least 10 minutes before moving them; the fruit topping needs time to set so it doesn’t slide off.

Flavor & Texture Notes

The standout feature of these cookies is the caramelized fruit contrast. The sugar cookie base is thick and buttery, providing a sturdy canvas for the juicy, tangy pineapple.

As the brown sugar melts in the oven, it creates a sticky, toffee-like ring around the fruit. The almond extract in the dough mimics the flavor of a traditional yellow cake, while the cherry adds a final bright, candy-like sweetness. It is a dense, satisfying cookie that feels like a mini-dessert in every bite.

Tips & Variations

• The Coconut Twist: Roll the edges of the dough balls in shredded coconut before flattening for a “Piña Colada” style cookie.
• Spice it Up: Add a half-teaspoon of ground ginger to the dough to complement the acidity of the pineapple.
• Fresh vs. Canned: Fresh pineapple provides a sharper flavor, but canned pineapple is often more consistent in sweetness and easier to pat dry.
• Glaze Option: If you want extra indulgence, whisk together a half-cup of powdered sugar with a teaspoon of pineapple juice and drizzle it over the cooled cookies.

Storage & Make-Ahead

• Refrigeration: Because of the fresh fruit topping, these cookies are best stored in the refrigerator in an airtight container for up to 3 days.
• Freezing: I do not recommend freezing these once baked, as the pineapple can become mushy upon thawing. However, you can freeze the unadorned dough balls for up to a month.
• Serving: These are excellent at room temperature, but 10 seconds in the microwave makes the pineapple topping warm and jammy again.

FAQ

Why did my cookies spread too much?

This usually happens if the butter was too warm or the pineapple wasn’t dried enough. Ensure your butter is “cool-room temperature” (it should hold an indent but not be greasy) and squeeze that pineapple dry!

Can I use pineapple rings instead of tidbits?

If you are making very large cookies, you can use small rings. For standard-sized cookies, tidbits or “chunks” cut into smaller pieces work best to ensure the dough-to-fruit ratio is balanced.

My pineapple fell off the cookie. What happened?

You need to press the fruit firmly into the dough before baking so the dough “grips” the fruit as it rises. If it still slides, try making a small indentation in the center of the dough disc before placing the fruit.

Conclusion

Pineapple Upside Down Sugar Cookies are a playful, sophisticated take on a classic flavor profile. They offer all the nostalgia of the traditional cake in a form that is easy to share and fun to eat. By focusing on high-quality extracts and properly prepared fruit, you create a cookie that is as beautiful as it is delicious.