These pineapple upside sugar cookies are a delightful twist on the classic pineapple upside-down cake. They combine the soft, buttery sweetness of sugar cookies with the tangy, caramelized flavor of pineapple and a cherry on top. Each bite feels like a mini tropical vacation.
Why You’ll Love This Recipe
I love how these cookies bring together the comfort of a sugar cookie and the nostalgia of a pineapple upside-down cake. I get the flavor of a retro dessert in a small, handheld treat that’s perfect for sharing. I also like how fun these look on a platter, with their glossy pineapple rings and bright cherries making them just as beautiful as they are tasty.
Ingredients
(Here's a tip: Check out the full list of ingredients and measurements in the recipe card below.)
Sugar cookie dough (homemade or store-bought)
Pineapple rings (canned, drained and patted dry)
Maraschino cherries
Brown sugar
Unsalted butter (melted)
Directions
I preheat my oven to 350°F (175°C) and prepare a muffin tin with non-stick spray.
I spoon about 1 teaspoon of melted butter and 1 teaspoon of brown sugar into the bottom of each muffin cup.
I place a pineapple ring into each cup, trimming them if needed so they fit nicely.
I add a maraschino cherry in the center of each pineapple ring.
I press a ball of sugar cookie dough on top of the pineapple and cherry, flattening slightly.
I bake for 12–15 minutes, until the cookies are golden and set.
I let the cookies cool in the pan for about 5 minutes before carefully flipping them out onto a baking sheet to cool completely.
Servings and timing
This recipe makes about 12 cookies, depending on the size of your muffin tin. It takes around 15 minutes of prep and 15 minutes of baking, so I usually have them ready to serve in about 30 minutes.
Variations
I like to swap the sugar cookie dough for shortbread dough when I want a richer base. Sometimes I add a sprinkle of shredded coconut to the brown sugar layer for extra tropical flavor. For a fun twist, I also make them in mini muffin tins with pineapple tidbits instead of rings for bite-sized versions.
storage/reheating
I store these cookies in an airtight container at room temperature for up to 3 days. If I want to keep them longer, I refrigerate them for up to 5 days. To reheat, I warm them in the microwave for 10–15 seconds, which brings back the gooey caramelized flavor.
FAQs
Can I use fresh pineapple instead of canned?
Yes, I can use fresh pineapple, but I make sure to slice it thinly and remove excess juice so the cookies don’t get soggy.
Do I have to use a muffin tin?
I prefer a muffin tin because it helps the pineapple and cherry stay in place, but I can also use a parchment-lined baking sheet with pineapple cut into smaller pieces.
Can I freeze these cookies?
Yes, I can freeze them once they’ve cooled completely. I place them in a single layer in a freezer-safe container and they’ll last up to 2 months.
What can I use instead of maraschino cherries?
I sometimes swap them for fresh cherries, cranberries, or even small raspberries if I want a less sweet option.
How do I stop the cookies from sticking to the pan?
I make sure to spray the muffin tin well and allow the cookies to cool slightly before flipping them out. Using parchment paper rounds at the bottom also helps.
Conclusion
I enjoy how these pineapple upside sugar cookies bring together classic flavors in a fun, bite-sized way. They’re simple, quick to make, and always impress when I share them. Whether I make them for parties, family gatherings, or just a sweet treat for myself, they never last long on the plate.
These pineapple upside sugar cookies combine the sweet, buttery flavor of sugar cookies with caramelized pineapple and cherry for a fun, mini twist on the classic upside-down cake.
Ingredients
1 batch sugar cookie dough (homemade or store-bought)
12 pineapple rings (canned, drained, and patted dry)
12 maraschino cherries
12 tsp brown sugar
12 tsp unsalted butter, melted
Instructions
Preheat the oven to 350°F (175°C) and spray a muffin tin with non-stick spray.
Add 1 teaspoon of melted butter and 1 teaspoon of brown sugar to each muffin cup.
Place a pineapple ring into each muffin cup, trimming as needed to fit.
Add a maraschino cherry in the center of each pineapple ring.
Press a ball of sugar cookie dough on top of the pineapple and cherry, flattening slightly.
Bake for 12–15 minutes, until the cookies are golden and set.
Let cookies cool in the pan for 5 minutes, then carefully flip them onto a baking sheet to cool completely.
Notes
Swap sugar cookie dough with shortbread dough for a richer taste.
Add shredded coconut to the brown sugar layer for a tropical twist.
Use mini muffin tins with pineapple tidbits for bite-sized cookies.
Store in an airtight container for up to 3 days at room temperature or refrigerate up to 5 days.
Reheat in the microwave for 10–15 seconds to refresh the flavor and texture.
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