I can’t get over how these pineapple-topped sugar cookies turn out so buttery, glossy, and irresistible. One bite gives you that upside-down cake magic in the cutest cookie form.

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I’m obsessed with these Upside Down Cake Pineapple Sugar Cookies because they hit that sweet spot between chewy cookie and juicy pineapple bite. I love how the buttery base keeps things rich, while pineapple slices bring that bright, tangy pop that makes me immediately reach for another.

And that sticky brown sugar topping? Absolutely dangerous in the best way.

These cookies feel fun without trying too hard, like something I’d bring to a backyard party and then secretly hope nobody finishes. But honestly, I’d eat them straight from the tray.

No plate needed. Just sweet, glossy, pineapple-packed cookie chaos.

Total dessert trouble.

Ingredients

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Flour gives the cookies their soft, sturdy bite.
Not fancy, just necessary.
Baking powder helps them puff a little so they’re not flat and sad.
Salt keeps all that sweetness from going totally wild.
Butter brings the rich, tender crumb you’ll want in every bite.
Granulated sugar makes the cookies sweet, light, and a little crisp.
Brown sugar adds caramel vibes, especially with the pineapple topping.
The egg holds everything together and keeps the texture chewy.
Vanilla makes the dough taste warmer, like a real bakery cookie.
Milk softens the dough so it bakes up tender.
Pineapple brings juicy, tangy sweetness.
Basically, it’s the whole retro mood.
Melted butter and brown sugar make that sticky upside-down cake topping.
Cherries add color, sweetness, and that classic diner-dessert look.
Plus, coarse sugar gives a tiny sparkle and crunch if you’re feeling extra.

Ingredient Quantities

2 1/2 cups (312 g) all purpose flour

1 teaspoon baking powder

1/2 teaspoon fine salt

1 cup (227 g) unsalted butter, softened

1 cup (200 g) granulated sugar

1/4 cup (50 g) packed light brown sugar

1 large egg

1 teaspoon pure vanilla extract

2 tablespoons milk (whole or 2 percent)

1 (20 ounce) can pineapple slices in juice, drained (about 8 rings)

1/3 cup packed light brown sugar for topping

2 tablespoons melted butter for topping

12 maraschino cherries, drained and halved (optional)

Coarse or sanding sugar for sprinkling, optional

How to Make this

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1. Preheat oven to 350 F and line two baking sheets with parchment paper or silicone mats.

2. In a medium bowl whisk together 2 1/2 cups (312 g) all purpose flour, 1 teaspoon baking powder, and 1/2 teaspoon fine salt; set aside.

3. In a large bowl or stand mixer beat 1 cup (227 g) softened unsalted butter with 1 cup (200 g) granulated sugar and 1/4 cup (50 g) packed light brown sugar until light and fluffy, about 2 to 3 minutes.

4. Add 1 large egg, 1 teaspoon pure vanilla extract, and 2 tablespoons milk to the butter mixture and beat until combined, scraping the bowl as needed.

5. Gradually add the dry ingredients to the wet mixture and mix until a soft dough forms; do not overmix.

6. Drain 1 (20 ounce) can pineapple slices in juice and pat rings dry with paper towels; reserve about 8 rings for cookies. If using 12 cookies, you can trim rings or overlap small slices as needed. Also drain and halve 12 maraschino cherries if using.

7. Scoop dough by rounded tablespoon or use a small cookie scoop to form balls and place 2 inches apart on prepared sheets; gently flatten each ball to about 1/2 inch thick with your palm or the bottom of a glass.

8. Place one pineapple ring onto the center of each flattened cookie, pressing gently so the dough rises around the ring. In a small bowl combine 1/3 cup packed light brown sugar and 2 tablespoons melted butter and spoon or sprinkle about 1 teaspoon of this mixture into the center of each pineapple ring. Top each ring with a halved maraschino cherry if desired. Optionally sprinkle coarse or sanding sugar over the cookie edges for sparkle.

9. Bake for 12 to 15 minutes, or until the cookie edges are set and lightly golden. Let cool on the baking sheet for 5 minutes so the topping sets, then transfer cookies to a wire rack to cool completely.

Equipment Needed

1. Oven (preheated to 350 F)
2. Two baking sheets plus parchment paper or silicone baking mats
3. Medium and large mixing bowls
4. Whisk and rubber spatula
5. Stand mixer or hand mixer (or a sturdy wooden spoon if mixing by hand)
6. Measuring cups and spoons and a kitchen scale (optional for grams)
7. Cookie scoop or tablespoon and a small bowl for topping mixture
8. Can opener and paper towels for draining pineapple slices
9. Wire cooling rack

FAQ

Q: Can I make the dough ahead of time?

A: Yes. Wrap the dough in plastic and refrigerate up to 48 hours or freeze up to 1 month. Bring to firm but pliable before rolling and cutting.

Q: How do I prevent soggy cookies from the pineapple?

A: Pat pineapple slices very dry with paper towels and drain well. You can also blot the cut rings after slicing and briefly broil or dry them in the oven at low heat to remove extra moisture.

Q: My cookies spread too much. What went wrong?

A: Overly warm dough or not enough flour can cause spreading. Chill the dough for 30 to 60 minutes before baking and measure flour correctly by spooning and leveling into the cup or weighing it.

Q: Can I use fresh pineapple instead of canned?

A: Yes. Use ripe fresh pineapple cut into slices, drain and pat very dry. Because fresh pineapple can be juicier, dry it longer to avoid excess moisture on the cookies.

Q: How should I store leftovers?

A: Store at room temperature in an airtight container for up to 3 days. For longer storage, freeze baked cookies in a single layer on a tray, then transfer to a freezer bag for up to 2 months.

Q: Can I make these gluten free or dairy free?

A: For gluten free, substitute a 1-to-1 gluten free flour blend and chill the dough a bit longer. For dairy free, replace butter with a solid plant based butter and use nondairy milk. Texture may vary slightly.

Upside Down Cake Pineapple Sugar Cookies Recipe Substitutions and Variations

All purpose flour: 1 to 1 gluten free flour blend (measure cup for cup), whole wheat pastry flour (slightly denser, use as written), or pastry flour for a more tender cookie
Unsalted butter: salted butter (omit added salt in recipe), vegan stick butter (use same weight), or solid coconut oil (gives slight coconut note)
Granulated sugar: coconut sugar (1:1, darker flavor), superfine or caster sugar (for finer texture), or a 50/50 mix of granulated and powdered sugar to reduce spread
Large egg: flax egg (1 tablespoon ground flaxseed plus 3 tablespoons water, whisk and rest 5 minutes), applesauce (1/4 cup, may make cookies softer), or mashed banana (1/4 cup, adds flavor)

Pro Tips

1. Pat the pineapple rings bone dry with paper towels and let them sit on a rack for a few minutes before topping the cookies. Extra moisture is the main cause of soggy centers and spreading.

2. Chill the portioned dough for 10 to 15 minutes on the baking sheet before adding the pineapple. A slightly firmer dough will hold its shape better in the oven and create a nicer collar around the ring.

3. Press the dough up around the pineapple gently rather than flattening the fruit into the cookie. That creates a shallow well for the brown sugar-butter mix so the topping caramelizes without pooling.

4. Use room temperature butter and beat until light and fluffy, then scoop dough with a small cookie scoop for even size. Evenly sized cookies bake more uniformly and make it easier to time the caramelization just right.

Upside Down Cake Pineapple Sugar Cookies Recipe

Recipe by Samantha Dalling

0.0 from 0 votes

I can’t get over how these pineapple-topped sugar cookies turn out so buttery, glossy, and irresistible. One bite gives you that upside-down cake magic in the cutest cookie form.

Servings

servings

Calories

674

kcal

Equipment: 1. Oven (preheated to 350 F)
2. Two baking sheets plus parchment paper or silicone baking mats
3. Medium and large mixing bowls
4. Whisk and rubber spatula
5. Stand mixer or hand mixer (or a sturdy wooden spoon if mixing by hand)
6. Measuring cups and spoons and a kitchen scale (optional for grams)
7. Cookie scoop or tablespoon and a small bowl for topping mixture
8. Can opener and paper towels for draining pineapple slices
9. Wire cooling rack

Ingredients

2 1/2 cups (312 g) all purpose flour
1 teaspoon baking powder
1/2 teaspoon fine salt
1 cup (227 g) unsalted butter, softened
1 cup (200 g) granulated sugar
1/4 cup (50 g) packed light brown sugar
1 large egg
1 teaspoon pure vanilla extract
2 tablespoons milk (whole or 2 percent)
1 (20 ounce) can pineapple slices in juice, drained (about 8 rings)
1/3 cup packed light brown sugar for topping
2 tablespoons melted butter for topping
12 maraschino cherries, drained and halved (optional)
Coarse or sanding sugar for sprinkling, optional

Directions

Preheat oven to 350 F and line two baking sheets with parchment paper or silicone mats.
In a medium bowl whisk together 2 1/2 cups (312 g) all purpose flour, 1 teaspoon baking powder, and 1/2 teaspoon fine salt; set aside.
In a large bowl or stand mixer beat 1 cup (227 g) softened unsalted butter with 1 cup (200 g) granulated sugar and 1/4 cup (50 g) packed light brown sugar until light and fluffy, about 2 to 3 minutes.
Add 1 large egg, 1 teaspoon pure vanilla extract, and 2 tablespoons milk to the butter mixture and beat until combined, scraping the bowl as needed.
Gradually add the dry ingredients to the wet mixture and mix until a soft dough forms; do not overmix.
Drain 1 (20 ounce) can pineapple slices in juice and pat rings dry with paper towels; reserve about 8 rings for cookies. If using 12 cookies, you can trim rings or overlap small slices as needed. Also drain and halve 12 maraschino cherries if using.
Scoop dough by rounded tablespoon or use a small cookie scoop to form balls and place 2 inches apart on prepared sheets; gently flatten each ball to about 1/2 inch thick with your palm or the bottom of a glass.
Place one pineapple ring onto the center of each flattened cookie, pressing gently so the dough rises around the ring. In a small bowl combine 1/3 cup packed light brown sugar and 2 tablespoons melted butter and spoon or sprinkle about 1 teaspoon of this mixture into the center of each pineapple ring. Top each ring with a halved maraschino cherry if desired. Optionally sprinkle coarse or sanding sugar over the cookie edges for sparkle.
Bake for 12 to 15 minutes, or until the cookie edges are set and lightly golden. Let cool on the baking sheet for 5 minutes so the topping sets, then transfer cookies to a wire rack to cool completely.

Notes

Below you’ll find my best estimate of this recipe’s nutrition facts. Treat the numbers as a guide rather than a rule—great food should nourish both body and spirit. Figures are approximate, and the website owner assumes no liability for any inaccuracies in this recipe.