Pineapple Cherry Upside Down Cookies take everything you love about pineapple upside down cake and tuck it into buttery, handheld sugar cookies.
If you grew up with classic pineapple upside down cake, these cookies are going to feel like pure nostalgia in bite-size form. You get the same glossy pineapple and cherry topping, but instead of a slice of cake, there’s a soft, rich sugar cookie holding everything together.
They’re just the kind of treat you’ll want for parties, potlucks, or holiday trays—easy to share, easy to transport, and impressive enough that people always ask for the recipe. The best part? You’re working with simple pantry ingredients and a straightforward method that rewards you with bakery-style results.
Because everything bakes in muffin tins, each cookie comes out looking like its own little mini cake—caramelized fruit on top, buttery cookie underneath, and a gorgeous shine that makes them look far more complicated than they really are. Once you try them, you might find yourself keeping pineapple and cherries on standby just so you can whip up a batch any time the craving hits.
What You Need to Make This Pineapple Cherry Upside Down Cookies
Unsalted butter (melted and softened) – Melted butter combines with brown sugar for that sticky, caramel-like topping, while softened butter gives the cookie base its tender, rich crumb.
Light brown sugar – Creates a quick caramel layer in the muffin cups, helping the pineapple and cherries turn glossy, sweet, and lightly sticky as they bake.
Pineapple rings – Halved rings nestle perfectly into muffin cups, bringing juicy, tropical sweetness. Canned pineapple is convenient, but well-drained fresh pineapple works beautifully too.
Maraschino cherries – Classic, bright-red cherries add color and a pop of fruity sweetness right in the center of each cookie.
Granulated sugar – Sweetens the cookie dough and helps it cream with the butter for that soft, tender sugar cookie texture.
Large egg – Binds the dough together and adds richness so the cookies stay soft, not crumbly.
Pure vanilla extract – Rounds out the flavors, adding warm bakery-style notes that pair perfectly with pineapple and cherry.
All-purpose flour – Provides structure for the sugar cookie base so it’s sturdy enough to support the juicy topping while still staying soft.
Baking powder and baking soda – A small combo of leaveners helps the cookie dough rise gently and bake up fluffy rather than dense.
Salt – Just a pinch balances the sweetness and keeps the flavors from tasting flat.
Pineapple juice – A splash of juice from the can (or fresh) adds moisture and intensifies the tropical notes in the cookie dough.
Step-by-Step Pineapple Cherry Upside Down Cookies
STEP 1: Preheat your oven to 350°F (175°C). Lightly grease two 12-cup muffin tins or line them with parchment liners to help the cookies release easily after baking.
STEP 2: Stir the melted butter and brown sugar together until smooth. Spoon about a teaspoon of this mixture into the bottom of each muffin cup, spreading it slightly so it covers the base.
STEP 3: Nestle a pineapple half on top of the sugar mixture in each cup, trimming if needed so it sits comfortably. Place one maraschino cherry in the center of each pineapple piece, pressing it down gently.
STEP 4: For the cookie dough, beat the softened butter and granulated sugar together until light and fluffy, about 2 minutes. Mix in the egg, vanilla, and pineapple juice, scraping down the bowl so everything is well combined.
STEP 5: In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Add the dry ingredients to the wet mixture in stages, mixing just until a soft, slightly sticky dough forms.
STEP 6: Roll portions of dough into roughly 1½-inch balls, then gently flatten them into thick discs with your hands. Place one disc over each fruit-filled muffin cup and press lightly so it reaches the edges without squashing the fruit underneath.
STEP 7: Bake for 11–13 minutes, or until the cookie edges are just turning golden and the centers look set. Avoid overbaking so the cookies stay soft after they cool.
STEP 8: Let the cookies cool in the pans for about 5 minutes. Carefully invert each pan over a baking sheet or cooling rack, giving it a gentle tap so the cookies release and the pineapple-cherry topping ends up on top. Cool fully before serving to let the caramel topping set.
Pro Tips for Pineapple Cherry Upside Down Cookies
- Use well-drained fruit
Pat the pineapple and cherries dry with paper towels so the topping thickens nicely instead of turning watery in the muffin cups. - Don’t overwork the dough
Mix the dry ingredients in just until combined. Overmixing can make the cookie base tough instead of soft and tender. - Invert while still warm
If the pans cool too much, the topping can stick. Invert after about 5 minutes, and if needed, run a knife around the edges to help them release.
Can I use canned pineapple instead of fresh?
Yes, canned pineapple rings work perfectly. Just drain them well and pat them dry. The reserved juice is great in the cookie dough for extra flavor and moisture.
Can I make these cookies ahead of time?
You can bake them a day ahead and store them covered in the fridge. Let them sit at room temperature for 20–30 minutes before serving, or warm briefly in a low oven.
Why did my topping stick to the muffin pan?
Usually it’s from cooling too long or not greasing the cups enough. Next time, grease well, invert after about 5 minutes, and loosen the edges with a small spatula if needed.
Can I use a sugar cookie mix instead of homemade dough?
Yes, a prepared sugar cookie mix can work in a pinch. Prepare the dough as directed on the package, then use it in place of the homemade dough for a shortcut version.
How do I know when the cookies are done?
Look for lightly golden edges and centers that look set but not dry. The cookies will firm up as they cool, so pull them out before they turn dark brown.
Serving Ideas for Pineapple Cherry Upside Down Cookies
These cookies are showy enough to stand alone on a dessert platter, but they’re also lovely paired with simple sides. A scoop of vanilla ice cream turns them into mini plated desserts without any extra effort.
For a party spread, place them alongside other bite-sized treats like brownies or bar cookies to add color and variety. Their glossy pineapple and cherry tops look gorgeous on holiday trays, Easter buffets, or summer cookouts.
If you want to play up the tropical angle, serve them with fresh fruit like strawberries, kiwi, or mango on the side. A little whipped cream or a drizzle of coconut-flavored cream is a fun extra for more indulgent occasions.
Keeping Leftovers Fresh
Because of the juicy fruit topping, these cookies keep best in an airtight container in the refrigerator. Arrange them in single layers with parchment between them so the tops don’t stick to one another.
Stored this way, they’re at their best within 3–4 days. Let chilled cookies sit at room temperature for about 20 minutes before serving so the cookie base softens and the flavors come forward again.
If you’d like to freeze them, place cooled cookies on a baking sheet to freeze solid, then transfer to a freezer-safe container or bag with parchment between layers. Freeze for up to 2 months. Thaw in the fridge overnight, then bring to room temperature, or warm briefly in a low oven just until the toppings regain their shine and the cookie centers are soft.
Pineapple Cherry Upside Down Cookies
Ingredients
For the fruit topping:
- 12 maraschino cherries thoroughly drained
- 6 circular pineapple slices halved (fresh or from a can)
- 4 tablespoons melted unsalted butter
- 8 tablespoons light brown sugar firmly packed
For the cookie dough:
- 1/2 teaspoon baking powder
- 1/2 cup pineapple juice preferably from the canned fruit or freshly squeezed
- 1 large egg
- 1 teaspoon vanilla extract
- 1 cup granulated sugar
- 1/4 teaspoon baking soda
- 1/4 teaspoon fine salt
- 2 sticks 1 cup unsalted butter, softened to room temperature
- 2 1/4 cups plain all-purpose flour
Instructions
- Preheat the oven to 350°F (175°C) and lightly coat two 12-cup muffin pans with nonstick spray or line with paper cups.
- For the topping, stir the melted butter together with the brown sugar in a small bowl until well blended. Spoon 1 teaspoon of the sugar-butter mixture into the base of each muffin cup.
- Place a halved pineapple ring over the sugar in each cup, then nestle a maraschino cherry in the center of the ring.
- To prepare the dough, beat the softened butter and granulated sugar in a large mixing bowl until the texture is airy and light, about 2 minutes.
- Incorporate the egg, vanilla, and pineapple juice into the creamed mixture, mixing just until combined.
- In a separate bowl, whisk together the flour, baking powder, baking soda, and salt until evenly distributed.
- Gradually incorporate the dry mixture into the wet ingredients, stirring until a cohesive and soft dough develops.
- Form the dough into balls roughly 1 1/2 inches in diameter. Lightly press each ball into a disc and set it atop the pineapple in the muffin tins, applying gentle pressure.
- Bake for 11 to 13 minutes, or until the edges of the cookies begin to turn golden.
- Once removed from the oven, allow the cookies to cool in the tins for 5 minutes. Then, carefully invert the pans over a wire rack or baking sheet so the fruit layer is on top.
- Let the cookies cool completely before serving to ensure the topping is set and stable.