Pineapple Upside Sugar Cookies

Soft, Buttery Cookies Topped with Juicy Pineapple & Gooey Brown Sugar Goodness

If you love classic pineapple upside-down cake but want something easier, cuter, and totally snackable, these Pineapple Upside Sugar Cookies are about to become your new favorite dessert. They’re soft, buttery sugar cookies topped with caramelized pineapple, a touch of brown sugar, and a cherry in the middle for that perfect retro look.

These cookies taste like tiny upside-down cakes — tender in the center, slightly chewy around the edges, and bursting with tropical sweetness in every bite. They’re easy enough for weeknight baking but pretty enough for parties, potlucks, and holiday trays.

If you already love making upside-down desserts, just wait until you try them in handheld cookie form. No slicing, no messy pans — just pop, bake, flip, and enjoy!

Ingredients

For the Sugar Cookies

1 cup unsalted butter, softened
1 cup granulated sugar
1 egg
1 tsp vanilla extract
2 ½ cups all-purpose flour
1 tsp baking powder
½ tsp baking soda
¼ tsp salt

For the Pineapple Topping

1 cup pineapple tidbits (fresh or canned, drained well)
½ cup brown sugar
¼ cup melted butter
Maraschino cherries (whole or halved)

Directions

1. Prepare Your Muffin Pan

The magic behind these cookies is baking them upside-down in a muffin tin — this gives them that perfect caramelized top.

Spray a 12-cup muffin tin generously with nonstick spray.

In each cup, add:

½–1 teaspoon melted butter
½–1 teaspoon brown sugar
4–6 pineapple tidbits
1 maraschino cherry (centered)

Set the pan aside while you make the cookie dough.

2. Make the Cookie Dough

In a large bowl, cream together the softened butter and sugar until light and fluffy.
Beat in the egg and vanilla extract until smooth.

In a separate bowl, combine flour, baking powder, baking soda, and salt.
Add the dry ingredients to the wet mixture and mix until a soft dough forms.

If the dough feels sticky, refrigerate it for 20 minutes — chilled dough bakes thicker and holds its shape better.

3. Shape & Add to the Pan

Scoop dough into 12 equal portions and roll into balls.
Press each dough ball gently into the muffin cups right on top of the pineapple mixture.
The dough doesn’t need to touch the edges; it will spread as it bakes.

4. Bake

Bake at 350°F (175°C) for 13–16 minutes, or until the edges appear set and lightly golden.

Allow cookies to rest in the pan for 5 minutes, then run a knife around the edges to loosen.

5. Flip & Reveal

Place a baking sheet over the muffin pan and flip carefully to release the cookies.

Lift the muffin tin away — and reveal perfect little pineapple upside cookies with a glossy, caramelized top!

Let cool completely before storing.