Pineapple Upside Sugar Cookies

These pineapple upside sugar cookies are pure sunshine on a plate. They combine buttery sugar cookie dough with juicy pineapple slices right on top. It is like the best of pineapple upside-down cake but in a fun hand-held treat that is so easy to share. The sugar on top gets crackly after baking and the pineapple turns even sweeter and just a little caramelized.

I always pull out this recipe when I crave something nostalgic but do not want hours in the kitchen. The first time I brought these to a potluck, they disappeared long before dessert was served.

Ingredients

• Unsalted butter: The foundation for a rich smooth dough that bakes up tender and flavorful Use a good-quality stick butter for best results
• Granulated sugar: For sweetness and just the right texture inside and a crisp crackle on top Choose fine pure cane sugar for best bakery style results
• Large egg: Binds the dough and helps the cookies rise I use local farmers market eggs when I can
• Vanilla extract: Adds warmth and depth to the cookie flavor Always reach for pure vanilla if possible
• All-purpose flour: Gives structure and stability Measure using the spoon and level method for accuracy
• Baking soda: Keeps the cookies light and perfectly soft Look for a fresh box with no lumps
• Salt: Balances the overall sweetness and sharpens flavors Opt for fine sea salt for even distribution in the dough
• Canned pineapple rings: The star of the show Look for slices packed in juice rather than syrup Drain and pat very dry so your cookies will bake up sturdy and not soggy
• Extra granulated sugar: A final sprinkle before baking gives a classic sugary sparkle Use a light touch for best results

Instructions

Make the Dough:

Cream butter and sugar together with an electric mixer on medium speed until the mixture looks fluffy and pale This takes three or four minutes and gives your cookies the perfect tender bite

Add Wet Ingredients:

Beat in the egg and vanilla until the dough is completely smooth and everything is combined well Scrape the sides of the bowl while mixing to make sure nothing sticks

Mix Dry Ingredients:

In a separate bowl whisk flour baking soda and salt to blend and remove clumps Gradually add this flour mixture to the wet ingredients Stir just until a soft even dough forms Do not overmix or cookies can be tough

Shape and Prepare:

Scoop one and a half tablespoons of dough and roll into balls Place on parchment lined baking sheets leaving a little space so cookies have room to spread Flatten each into a disk about as wide as the pineapple ring

Add Pineapple:

Set a well drained pineapple ring on top of each dough disk and press gently so the fruit is nestled but not squished in

Sugar Sprinkle:

Lightly sprinkle the top of each pineapple ring with extra sugar for a glossy finish and a little sweet crunch after baking

Bake:

Bake at three hundred fifty degrees Fahrenheit for twelve to fourteen minutes Watch for the edges to turn just golden and the cookies look set in the middle This timing keeps the cookies chewy yet sturdy

Cool:

Let the cookies cool on the baking sheet for five minutes so they firm up before transferring to a wire rack to cool completely If moved too soon the cookies can break under the juicy pineapple

The canned pineapple rings are always a hit at my house My daughter loves helping to pat them dry before we bake Her little fingers are perfect for the job and it always turns into a giggle fest

Storage Tips

Store cooled cookies in an airtight container at room temperature for up to three days For longer freshness refrigerate and let come to room temperature before serving The pineapple topping keeps the cookies moist so they are still great days later

Ingredient Substitutions

You can swap pineapple rings for fresh pineapple slices but be sure to cut them thin and drain even more liquid If you want another flavor try peach rings or maraschino cherries as a nod to classic upside down cake Both options give their own twist and look festive

Serving Suggestions

Dust the cookies with extra sugar after baking for extra sparkle I love to serve these with black tea or a toasted coconut latte They are lovely as part of a dessert buffet or wrapped up to share with neighbors

Cultural and Historical Context

These cookies draw inspiration from the old fashioned pineapple upside down cake which was especially popular in the mid twentieth century It became an American classic because canned pineapple was a novelty and made it easy to bake an exotic dessert at home The cookie version brings all that retro fun in a more casual format

Seasonal Adaptations

Use fresh pineapple in summer when it is super sweet and ripe For winter holidays add a dash of cinnamon to the dough Try a heart shaped cookie cutter for Valentine gatherings

Success Stories

Friends always text me for this recipe after tasting them These cookies brought rave reviews to a baby shower last spring and I love seeing everyone light up at both the look and taste They make any table feel more festive

Freezer Meal Conversion

You can freeze the cookie dough balls on a tray then transfer to a zip top bag and freeze up to three months When you are ready to bake just thaw as many as you need then flatten and top with pineapple right before they go in the oven

These cookies come together in a flash and always leave everyone smiling. Enjoy them fresh for best texture, but they are just as delightful the next day.

Recipe FAQs

→ How do I prevent the cookies from getting soggy?

Pat pineapple rings very dry before placing on the dough to minimize extra moisture for crisp results.

→ Can I use fresh pineapple instead of canned?

Yes, slice fresh pineapple into thin rings and pat dry thoroughly to maintain cookie texture.

→ Why sprinkle sugar on top before baking?

The extra sugar caramelizes in the oven, adding a sparkly, crisp finish to the pineapple and cookie.

→ Is chilling the dough required?

Chilling is not necessary here, as the dough is designed for immediate shaping and baking.

→ Can these cookies be made ahead?

They keep well in an airtight container for up to 3 days; the texture stays soft with a citrusy aroma.