Pineapple Upside Down Sugar Cookies sunny, buttery, and perfect for sharing

Introduction

These pineapple upside down sugar cookies capture the warm nostalgia of the classic cake in a handheld, golden cookie. Soft, buttery sugar dough hugs a glossy pineapple ring that caramelizes slightly at the edges for a little tropical surprise. They bake quickly and present beautifully for parties, picnics, or an easy gift in a cookie tin. If you love reinvented classics, pair them with other playful cookies like brown sugar pop tart cookies for a bright dessert spread.

Why This Recipe Is a Great Choice

There is something instantly cheerful about a cookie topped with a pineapple ring. These cookies are visually striking without fussing over decorations the fruit does all the work. The straightforward dough comes together in minutes, so you can shape and top dozens in a single baking session. They are kid friendly to assemble, making them a fun weekend activity that yields bakery-worthy results. Because the pineapple is canned and prepped, they’re a reliable option year round whether fresh fruit is in season or not. Try serving them on a pretty platter for an instant centerpiece or tuck a few into tissue for edible gifts. For another nostalgic twist to serve alongside, consider the light creaminess of Boston cream pie cookies to round out the spread.

Flavor and Texture

The base cookie is rich with butter and lightly sweetened, creating a tender crumb that melts on the tongue. The edge of each cookie crisps just enough to contrast the soft center while the pineapple adds a juicy pop and gentle acidity. A sprinkle of extra sugar on top gives a glittering, caramelized finish that catches the light and adds crunch. Vanilla and the butter’s toasted notes keep the flavor homey and familiar, balancing the tropical brightness. Overall these cookies land between a classic sugar cookie and a tender shortbread with a tropical crown.

Ingredients

– 1 cup unsalted butter, softened
– 1 cup granulated sugar
– 1 egg
– 1 tsp vanilla extract
– 2½ cups all-purpose flour
– ½ tsp baking soda
– ¼ tsp salt
– 10–12 canned pineapple rings, well-drained and patted dry
– Additional sugar for sprinkling

Step by Step Instructions

1. Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
2. In a large bowl, cream butter and sugar until light and fluffy.
3. Beat in the egg and vanilla until well combined.
4. In a separate bowl, whisk together flour, baking soda, and salt. Gradually add to the butter mixture to form a soft dough.
5. Roll dough into 1½ tbsp balls, flatten slightly, and place on baking sheet.
6. Top each dough disk with a pineapple ring, pressing gently.
7. Sprinkle sugar on top of pineapple for extra sparkle.
8. Bake 12–14 minutes until edges are golden.
9. Cool 5 mins, then transfer to a rack.

Tips for Best Results

Work with room temperature butter so the dough creams smoothly and traps air for a lighter texture. Pat the canned pineapple dry to prevent soggy cookies and to help the sugar on top caramelize instead of dissolving. Use a small scoop to portion dough evenly so cookies bake at the same rate and look uniform on the tray. If you like a deeper caramel color, sprinkle a little brown sugar on the pineapple in addition to granulated sugar. Rotate your baking sheet halfway through the bake if your oven has hot spots to keep every cookie evenly golden.

Storage and Make Ahead

Store cooled cookies in an airtight container at room temperature for up to three days for best texture. For longer storage, freeze unbaked dough balls on a tray until firm, then transfer to a freezer bag; bake from frozen, adding a minute or two to the bake time. Baked cookies also freeze well; thaw on the counter for 30 minutes to return to a tender bite. Avoid refrigerating, which can dry the cookies out quickly.

Final Thought

These pineapple upside down sugar cookies are an effortless way to bring sunshine to any gathering. They look like you spent hours while being delightfully simple to make. Keep a can of pineapple on hand and you’ll always have a quick crowd-pleaser at the ready.

Conclusion

For a tried and tested inspiration for this playful twist on a classic, see Pineapple Upside Down Sugar Cookies – Cookie Dough and Oven for additional photos and variations.

FAQ

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