I created these Delicious Pineapple Upside‑Down Sugar Cookies to capture the nostalgic charm of the classic pineapple upside‑down cake in a fun, handheld sugar cookie form. Soft yet crisp, each cookie features a buttery base topped with pineapple jam and a sugar-dusted pineapple slice for visual flair and tropical sweetness.

Why You’ll Love This Recipe

I love how these cookies combine a tender sugar cookie with the bright, caramelized flavor of pineapple. They’re easy to make, festive, and perfect as a twist on traditional cookies. Plus, the pineapple topping gives them a playful, eye-catching presentation without fuss.

Ingredients

(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

All‑purpose flour
Baking powder and a pinch of salt
Unsalted butter, softened
Granulated sugar
Egg
Vanilla extract
Pineapple jam or crushed pineapple (drained well)
Optional: small pineapple slices or rings for garnish
Extra granulated sugar or sanding sugar for rolling

Directions

I preheat the oven to 350 °F (175 °C) and line baking sheets with parchment.
I cream together softened butter and sugar until light and fluffy, then beat in the egg and vanilla.
I whisk together flour, baking powder, and salt, then gradually add to the wet ingredients until a smooth dough forms.
I chill the dough for about 30 minutes to firm up.
I scoop dough into balls (about 1½ tablespoons each), roll in granulated or sanding sugar, and place spaced on the prepared sheets.
I gently press down each dough ball and top with a dollop of pineapple jam or a small pineapple slice.
I bake for about 10–12 minutes, until edges just begin to turn golden. I let them rest on the sheet for a few minutes, then transfer to a rack to cool.

Servings And Timing

This recipe yields about 2 dozen cookies, depending on size.

Prep time: 15 minutes
Chill time: 30 minutes
Bake time: ~10–12 minutes
Total time: approximately 1 hour

Variations

I use crushed pineapple against the dough instead of jam for a more fruit-forward bite.
I swirl a cinnamon-sugar mix into the dough for warm spice notes.
I top with a maraschino cherry half for a colorful, retro vibe.
I sprinkle coarse sugar before baking for extra sparkle and crisp.
I make a chilled cream cheese glaze to drizzle over cooled cookies for added sweetness.

Storage/Reheating

I store these cookies in an airtight container at room temperature for up to 3 days, or in the fridge for 4–5 days if using fresh pineapple. I don’t recommend freezing because the pineapple topping may become watery—better to enjoy fresh or store in single layers to retain crispness.

FAQs

What Kind Of Pineapple Topping Works Best?

I prefer pineapple jam or preserves—they’re thick, sweet, and easier to manage. If using crushed pineapple, I drain it well or even cook it down slightly to reduce moisture.

Can I Make Dough Ahead Of Time?

Absolutely. I refrigerate the rolled dough balls for up to 24 hours before topping and baking—it helps intensify flavor and makes morning baking easy.

Will Cookies Spread Too Much?

Chilling the dough is key. I always chill at least 30 minutes before baking to keep the shape intact and control spread.

Can I Skip Topping the Cookies?

Yes—I sometimes bake plain sugar cookies and serve pineapple jam or fruit glaze on the side for dipping or spreading.

Are These Suitable for Parties?

Definitely. They transport well, look festive, and offer a fun flavor twist guests enjoy. Decorating with pineapple and sugar makes them stand out on cookie trays.

Conclusion

I love making these Pineapple Upside‑Down Sugar Cookies when I want something nostalgic, bright, and fun to bake. They bring the flavor of pineapple upside‑down cake to a simple cookie with minimal fuss. Soft yet fresh, sweet with tropical charm, they’re perfect for brunch, parties, or when craving something a little different—and completely delicious.