Pineapple Upside-Down Sugar Cookies are a delightful mini version of the classic pineapple upside-down cake. These individual treats are made with soft, buttery sugar cookie dough topped with caramelized pineapple rings and cherries. Perfectly portioned and packed with nostalgic flavor, they’re ideal for parties, bake sales, or anytime you want a tropical twist on a classic cookie.

Why You’ll Love This Recipe

A fun, bite-sized take on a retro dessert favorite
Combines soft sugar cookies with fruity, caramelized topping
No slicing required—perfect for serving at parties
Beautiful presentation with minimal effort
Easy to make with simple pantry ingredients

ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Sugar cookie dough (homemade or store-bought)
Pineapple rings, cut into smaller pieces or chunks
Maraschino cherries
Brown sugar
Butter
Nonstick spray or cupcake liners

directions

Preheat oven to 350°F (175°C). Grease a muffin tin or line with cupcake liners.
In a small bowl, mix melted butter and brown sugar. Spoon a small amount into the bottom of each muffin cup.
Place a piece of pineapple (or half a ring) on top of the brown sugar mixture. Add a maraschino cherry in the center.
Roll cookie dough into balls and gently press each one over the fruit layer, flattening slightly.
Bake for 12–15 minutes, or until the edges are golden and the cookie is set.
Allow to cool in the pan for about 5 minutes, then run a knife around the edges and invert onto a wire rack or tray to cool completely.
Serve warm or at room temperature.

Servings and timing

This recipe makes 12 cookies.
Prep Time: 15 minutes
Cook Time: 12–15 minutes
Total Time: ~30 minutes

Variations

Use crushed pineapple instead of rings for easier shaping
Add a splash of pineapple juice or rum extract to the cookie dough for extra flavor
Sprinkle a pinch of cinnamon or nutmeg over the brown sugar layer
Use a cream cheese sugar cookie dough for extra richness
Substitute the sugar cookie dough with shortbread dough for a different texture

storage/reheating

Store cookies in an airtight container at room temperature for up to 3 days.
To reheat, microwave for 10–15 seconds to revive the warm, gooey topping.
If freezing, wrap each cookie in plastic wrap and store in a sealed container for up to 1 month. Thaw before serving.

FAQs

Can I use canned pineapple?

Yes, canned pineapple rings or chunks work perfectly for this recipe.

Can I make these ahead of time?

Yes, they hold up well for a couple of days and can be made in advance.

What if I don’t have a muffin tin?

You can use ramekins or a mini cake pan, but a muffin tin helps keep the shape best.

Is homemade sugar cookie dough better than store-bought?

Homemade adds a personal touch, but store-bought works just fine for convenience.

Do I need to drain the pineapple?

Yes, pat it dry to prevent excess moisture from affecting the cookies.

Can I make these gluten-free?

Yes, use a gluten-free sugar cookie dough and check that all other ingredients are certified gluten-free.

Can I use fresh pineapple?

Yes, just slice it thinly and cut into pieces that fit in the muffin cups.

Do I need to flip the cookies immediately?

Let them cool for about 5 minutes first to set slightly, then flip while still warm.

Can I skip the cherry?

Absolutely. They’re traditional but optional—add an extra bit of pineapple or leave the space empty.

Can I make this recipe vegan?

Yes, use a vegan sugar cookie dough and plant-based butter to keep it dairy-free.

Conclusion

Pineapple Upside-Down Sugar Cookies are the perfect marriage of nostalgic flavor and modern convenience. With their golden caramel tops, tropical fruit, and soft cookie base, they’re a guaranteed crowd-pleaser. Whether you’re making them for a summer gathering or just to brighten up your day, these cookies bring big flavor in a small, irresistible package.