Chewy Pineapple Upside-Down Sugar Cookies
These soft sugar cookies carry all the sticky, caramelized charm of a classic pineapple upside-down cake. Each one bakes in a muffin cup so the brown sugar melts into a glossy glaze around the pineapple ring, and you get a perfect single serving every time.
If you want a dessert that feels a little nostalgic but is simple enough to pull off on a Tuesday, this is it.
Why These Cookies Work
The sugar cookie base stays tender under the warm fruit, and the edges crisp up just a little from the butter and brown sugar underneath. You get a soft center, a sticky top, and that bright pop of maraschino cherry right in the middle.
The recipe uses canned pineapple because it is reliably sweet and already the right size. Nothing fussy, no extras, just a quick dough and a few minutes in the oven.
Ingredients
- ½ cup unsalted butter, softened: let it sit on the counter for 30 minutes so it creams easily.
- ¾ cup granulated sugar: plain white sugar gives the cookie the right chew.
- 1 large egg: at room temperature if you remember, but cold works too if you beat it in slowly.
- 2 tsp vanilla extract: pure vanilla makes a difference here, but imitation is fine.
- 1 ¾ cups all-purpose flour: spooned and leveled, not scooped.
- 1 tsp baking powder: check the date, old baking powder can make the cookies dense.
- ¼ tsp salt: fine sea salt or table salt.
- ¼ cup butter, melted: for the topping, salted or unsalted both work.
- ⅓ cup packed light brown sugar: dark brown is okay too, the molasses flavor will be stronger.
- 10 canned pineapple rings, drained: from a 20 oz can, pat them dry with a paper towel.
- 10 maraschino cherries: stems removed, you can halve them if you prefer a smaller pop of color.
Variations / Substitutions
- Swap the pineapple: peach halves or pear slices from a can work the same way, just pat them dry.
- Go all vanilla: skip the brown sugar topping and use a dusting of powdered sugar after baking for a plainer sugar cookie with fruit.
- Make them gluten free: use a 1 to 1 gluten free baking flour blend instead of all-purpose, no other changes needed.
- No maraschino cherries: dried cranberries or a small dab of raspberry jam in the center give a similar sweet-sharp hit.
- Smaller treats: cut the rings in half and use mini muffin tins, then reduce the bake time by a couple of minutes.
Moist Vanilla Poke Cake is another reader favorite dessert worth making next.
How to Make Pineapple Upside-Down Sugar Cookies
Step 1: Cream the Butter and Sugar
Preheat your oven to 350°F (175°C) and grease every cup of a 12-cup muffin tin thoroughly, even the flat top between the cups, because the topping will bubble. In a large bowl, beat the ½ cup softened butter and ¾ cup granulated sugar with an electric mixer for about 2 minutes, until the mixture goes pale and looks like wet sand.
Scrape down the sides once or twice. You want no streaks of butter left, because any unmixed fat will melt out and make the cookies spread too much.
Step 2: Beat in the Egg and Vanilla
Crack the large egg right into the bowl and add the 2 teaspoons vanilla extract. Beat on low until the egg is fully incorporated and the batter smooths out, about 1 minute.
The mixture will look glossy and a little thicker now. A few tiny curdled bits are normal because the butter and egg are cold, they will disappear when you add the flour.
Step 3: Mix the Dough
Add the 1 ¾ cups flour, 1 teaspoon baking powder, and ¼ teaspoon salt to the bowl all at once. Stir with a wooden spoon or the mixer on low just until no dry pockets remain, roughly 30 seconds.
Stop as soon as the dough comes together. Overworking it makes the cookies tough, so keep it shaggy and soft. It will feel slightly greasy, not sticky.
Step 4: Assemble the Topping
Stir the ¼ cup melted butter and ⅓ cup brown sugar together right in a small bowl until it looks like wet sand. Spoon about a teaspoon of this mixture into the bottom of each greased muffin cup, then use your fingers or the back of the spoon to spread it into an even layer.
Press one pineapple ring into the center of each cup, on top of the brown sugar. Tuck a maraschino cherry into the hole in the middle of each ring.
Step 5: Add the Cookie Dough
Scoop a generous tablespoon of the dough and roll it into a ball, then flatten it slightly between your palms. Lay it on top of the pineapple ring so it covers the fruit mostly, but it is okay if some yellow peeks through the edges.
Repeat with the remaining dough, you should have exactly 10 balls. The dough will fill the cups about halfway, and it will rise and spread as it bakes.
Step 6: Bake and Flip
Set the tin in the center of your oven and bake for 14 to 16 minutes, until the cookie tops are set and just barely golden at the edges. Let the tin cool on a wire rack for exactly 5 minutes, no longer, because the caramel will start to harden and stick.
Run a thin knife around the edge of each cookie to loosen it, then place a baking sheet or large cutting board upside down over the tin. Holding both together, flip the whole thing over in one quick motion so the cookies drop out pineapple side up. Lift the tin off and serve warm.
Tips for the Best Pineapple Upside-Down Cookies
- Dry the pineapple rings really well. If they are too wet, the brown sugar will turn into a thin juice instead of a sticky glaze.
- Grease the tin generously, even the top flat surface. Once the sugar bubbles over it will stick and make the cookies hard to release cleanly.
- Do not let the cookies sit in the pan longer than 5 minutes. The brown sugar sets as it cools and glues the fruit to the pan.
- If a few cherries shift during the flip, just nudge them back into place while the topping is still warm.
Storing Leftovers
Keep the cookies in a single layer in an airtight container in the fridge for up to 4 days. The topping stays tacky, so put a piece of parchment between them if you stack them.
To serve again, warm them in a 300°F oven for 4 to 5 minutes until the sugar softens. A microwave works in a pinch, about 10 seconds, but the cookie loses a little of its chew.
Frequently Asked Questions
Can I use fresh pineapple instead of canned?
You can, but canned rings are cut to the right thickness and are reliably sweet and soft. Fresh pineapple tends to be firmer and can give off more juice, which will thin your glaze.
What should I do if the cookies stick in the pan?
Set the tin over a burner on very low heat for 30 seconds, or run a hot damp towel over the bottom of the tin. The heat will soften the hardened brown sugar so you can wiggle them out.
Why did my cookies come out dry?
Dry cookies usually mean the dough was overmixed or the flour was scooped too heavily. Next time, spoon the flour into the measuring cup and level it, and stop mixing as soon as the flour disappears.
Can I make the dough ahead of time?
Yes, you can wrap the dough ball in plastic and refrigerate it for up to 24 hours. Let it sit at room temperature for about 15 minutes before you roll and flatten it, so it is easy to work with.
Pineapple Upside-Down Sugar Cookies Recipe
Ingredients
Method
- Preheat oven to 350°F (175°C) and grease a 12-cup muffin tin well. Beat the softened butter and granulated sugar with an electric mixer for 2 minutes until pale and fluffy.
- Beat in the egg and vanilla until the mixture is smooth and glossy, about 1 minute.
- Add the flour, baking powder, and salt all at once and stir just until a soft dough forms, about 30 seconds.
- Stir the melted butter and brown sugar together, then spoon a teaspoon into the bottom of each muffin cup. Press a pineapple ring in and place a cherry in the center.
- Scoop a tablespoon of dough, roll it into a ball, flatten it, and lay it over each pineapple ring. You will have 10 dough balls.
- Bake for 14 to 16 minutes, until the cookies are set and just golden at the edges. Cool in the pan for 5 minutes, then invert onto a board and serve warm.
Notes
