Pineapple Upside Sugar Cookies are a whimsical riff on a retro classic, combining the sunny flavors of pineapple upside-down cake with the crisp, buttery delight of homemade sugar cookies. Each cookie is adorned with a caramelized pineapple-cherry topping and a golden, chewy base, making them both visually stunning and outrageously delicious.
This bake bridges generations: it’s comfort food for old souls, playful enough for kids, and sophisticated enough to grace a holiday dessert platter or summer picnic. With this recipe, nostalgic dessert meets handheld ease, and the result is an edible sunshine that brings joy to any occasion.
Why You’ll Love It
These cookies deliver everything that makes pineapple upside-down cake beloved—the contrast of juicy, tart fruit and sweet, caramelized edges—while adding the craveworthy texture of a sugar cookie. The cookie base provides a rich, sturdy canvas for juicy pineapple and glossy maraschino cherries, with hints of brown sugar and vanilla throughout.
They’re easy to bake in batches, keep well for sharing or gifting, and never fail to elicit a smile thanks to their brilliant appearance. The playful, retro twist also makes them a natural fit for themed parties, bake sales, and whimsical treats for kids or nostalgic adults.
Key Ingredients
- 2 1/2 cups all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup unsalted butter, room temperature
- 1 cup granulated sugar
- 1/3 cup brown sugar (light or dark)
- 2 large eggs
- 2 teaspoons vanilla extract
- 1/2 teaspoon almond extract (optional)
- 1/2 cup crushed pineapple, well drained (plus more for topping)
- 12–18 maraschino cherries, halved
- 1/3 cup pineapple preserves or extra crushed pineapple for topping
- 1/4 cup brown sugar (for caramelized topping)
- 2 tablespoons unsalted butter, melted (for topping)
- Optional: toasted coconut, pecans, or pearl sugar for garnish
Preparation
Start by thoroughly draining the crushed pineapple, pressing it between paper towels to remove excess juice—this keeps the cookies crisp and prevents spreading. In a medium bowl, whisk flour, baking powder, baking soda, and salt together.
In a large bowl, cream the butter, granulated sugar, and brown sugar until light and fluffy. Beat in eggs one at a time, then vanilla and almond extracts. Add the well-drained crushed pineapple and mix gently to combine. Gradually add the dry ingredients, mixing just until a thick dough forms.
Cover and chill dough for at least 1 hour; this helps manage the moisture and makes scooping easier.
Preheat oven to 350°F (175°C) and line two baking sheets with parchment. For the topping, stir pineapple preserves (or extra drained pineapple), brown sugar, and melted butter in a small bowl. Set out cherry halves.
To assemble, scoop 2 tablespoons of chilled dough into balls and place well spaced on sheets. Press each ball into a thick disc, making a small indent in the center. Spoon a small amount of pineapple-sugar topping and nestle a cherry half into the cavity.
Bake 12–15 minutes, until cookies are puffed, edges golden, and pineapple bubbly. Cool on sheets for 5 minutes then transfer to racks. Garnish with toasted coconut, chopped pecans, or extra sugar for flair.
Technique, Tips & Tricks
For the best shape and texture, chill dough thoroughly and use a cookie scoop for uniform rounds. Pressing an indent helps keep the topping from running off. Drain pineapple very well—excess moisture leads to flat, soft cookies rather than chewy-bite ones.
If using fresh pineapple, dice finely and drain even longer. For extra caramelization, sprinkle a pinch of brown sugar on top halfway through baking. Maraschino cherries give classic color, but candied pineapple or dried cherries work for variations.
Don’t overbake—the goal is chewy, just-set edges with a softer middle. Cookies keep best stored single layer or with parchment between layers to keep fruit topping neat.
Substitutions and Variations
Make gluten-free cookies by using a GF flour blend. For dairy-free, use vegan butter alternatives. Swap almond extract for coconut extract for a tropical twist, or fold in a handful of toasted coconut to the dough.
Try different fruit toppings: mango, peaches, or apricots lend summer flair, while pears are lovely for fall. Add a sprinkle of cinnamon to filling for warmth, or drizzle with white chocolate for special occasions.
Make mini versions for parties or larger “cookie cakes” for easy slicing. Instead of pineapple preserves, use apricot jam for complementary sweetness.
Serving Suggestions
Serve Pineapple Upside Sugar Cookies on a tray with fresh fruit, iced tea, or lemonade at a summer gathering, or alongside holiday desserts with hot cocoa or coffee. Their golden, caramelized tops add cheer to any dessert table.
Gift cookies in decorative tins, separated by parchment for neatness. For brunch, pair with yogurt parfaits and citrus salad. Mix into ice cream or chop and layer inside trifles for a fun, deconstructed cake experience.
Render extra indulgent by serving warm with whipped cream or vanilla ice cream as a plated dessert.
Story & Origins
These cookies borrow from the century-old tradition of pineapple upside-down cake—a classic American dessert popular since the early 1900s, when canned pineapple became widely available. The marriage of caramelized fruit and cake lent itself easily to playful spins, and sugar cookies became the perfect portable medium for these sunny flavors.
Bakers and bloggers gave the treat new life in the past decade, creating handheld versions for parties, bake sales, and creative dessert tables. The nostalgia and visual charm keep these cookies relevant and beloved, as they evoke cozy memories and playful celebrations.
Nutrition Notes
Each cookie packs carbs and sugar, with a touch of fiber from fruit and potential vitamins depending on the fruit and add-ins. Lighter versions are easy—use less sugar, whole grain flour, or swap some butter for applesauce.
Gluten- and dairy-free adaptations work well with modern baking supplies.
Their portioned size makes them ideal for mindful indulging. Topping them with extra fruit instead of sugar or nuts yields a more nutritious treat.
Flavors & Pairings
Pineapple pairs beautifully with coconut, citrus, and vanilla—serve cookies with fresh orange segments, pineapple punch, or a coconut macaroon for maximum tropical comfort.
They complement pistachio ice cream, tangy lemon bars, or a simple fruit salad.
For drinks, iced tea, pineapple juice, or sparkling water matches the sunny mood.
Frequently Asked Questions
Can I use fresh pineapple?
Yes—just dice finely, drain well, and blot before mixing.
Can I freeze them?
Yes—freeze baked cookies in layers, thaw and refresh in a warm oven.
How do I prevent cookie spreading?
Chill dough well, drain pineapple thoroughly, and avoid overmixing.
Can I use jam instead of preserves?
Absolutely—apricot, peach, or pineapple jams work beautifully.
Are these cookies suitable for kids’ baking?
Yes—easy to assemble, decorate, and eat.
How long do they keep?
Up to 5 days airtight; for longer storage, freeze.
Final Thoughts
Pineapple Upside Sugar Cookies are the delightful blend of retro nostalgia and modern fun—offering golden, chewy comfort with every caramelized bite. Whether shared at picnics, given as gifts, or enjoyed with family for dessert, these cookies bring sunshine and smiles year-round.
