These Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic pineapple upside-down cake, transformed into individual servings of chewy, fruity goodness. With caramelized pineapple and cherry topping baked right into a soft sugar cookie base, each bite is a delicious combination of tropical flavor and comforting sweetness.

Why You’ll Love This Recipe

These cookies are perfect for parties, potlucks, or anytime you want a tropical treat in a fun and portable form. They combine the nostalgic taste of pineapple upside-down cake with the ease and convenience of cookies. Plus, they look impressive and taste even better.

ingredients

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

Canned pineapple slices
Maraschino cherries
Brown sugar
Unsalted butter
Granulated sugar
Eggs
Vanilla extract
All-purpose flour
Baking powder
Salt

directions

Preheat your oven to 350°F (175°C). Grease a muffin tin or line with non-stick spray.
Cut pineapple slices into small pieces to fit the bottom of each muffin cup. Place a few chunks or half a slice in each, followed by a halved maraschino cherry in the center.
Sprinkle a spoonful of brown sugar and a small dab of butter on top of the fruit in each muffin cup.
In a bowl, cream together the butter and sugar until fluffy. Add in the eggs and vanilla extract and mix well.
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture until a soft dough forms.
Scoop a spoonful of cookie dough and flatten it slightly, then press it over the fruit mixture in each muffin cup.
Bake for 15–18 minutes, or until the cookies are golden around the edges.
Let them cool in the pan for 5 minutes before carefully inverting the muffin tin onto a tray to release the cookies.
Serve warm or allow to cool completely.

Servings and timing

This recipe makes about 12 cookies.
Prep time: 20 minutes
Cook time: 15–18 minutes
Total time: Approximately 40 minutes

Variations

Add a pinch of cinnamon or nutmeg to the dough for a spiced version.
Use fresh pineapple if desired, but make sure to pat it dry.
Substitute coconut sugar for a more caramel-like flavor.
Add a teaspoon of coconut extract to the dough for extra tropical flair.
Try making mini versions in a mini muffin pan for bite-sized treats.

storage/reheating

Store cooled cookies in an airtight container at room temperature for up to 3 days.
Refrigerate for longer storage, up to 5 days.
To reheat, warm in the microwave for 10–15 seconds or in a low oven at 300°F (150°C) for 5–7 minutes to re-caramelize the top.

FAQs

How do I prevent the cookies from sticking to the pan?

Make sure to generously grease your muffin tin or use non-stick spray. Let the cookies cool slightly before inverting.

Can I use fresh pineapple instead of canned?

Yes, just be sure to cut it into small pieces and pat it dry to prevent excess moisture.

Do I need to use maraschino cherries?

While traditional, you can skip them or replace with dried cherries or berries for a different flavor.

Can I freeze these cookies?

Yes, freeze them in a single layer and store in a freezer-safe bag for up to 2 months. Reheat before serving.

Can I use store-bought sugar cookie dough?

Yes, to save time, store-bought dough can be used, though homemade has a better texture and flavor.

Why did my cookies fall apart?

They may not have cooled enough before removing from the pan. Let them sit for at least 5 minutes.

What if I don’t have a muffin tin?

You can use ramekins or make them flat on a baking sheet, but the shape and topping may differ.

Can I make these gluten-free?

Yes, use a 1:1 gluten-free flour substitute that’s suitable for baking.

Are these cookies overly sweet?

They are rich and sweet due to the caramelized topping. You can reduce the sugar slightly in the dough if preferred.

Can I make these ahead of time?

Yes, they store well and can be made a day or two in advance. Just reheat before serving if you want the topping gooey again.

Conclusion

Pineapple Upside-Down Sugar Cookies offer a fun and flavorful way to enjoy a classic dessert in cookie form. Whether you’re making them for a gathering or simply to satisfy a craving, these cookies are sure to impress with their vibrant look and rich, tropical taste.