Pineapple Upside Down Sugar Cookies Recipe

If you’re looking for a show-stopping treat that pairs classic comfort with a pop of tropical fun, these Pineapple Upside Down Sugar Cookies are about to steal your dessert-loving heart. Imagine a buttery, soft sugar cookie base topped with sweet, caramelized pineapple rings baked right in—each bite is the perfect balance of tender crumb and juicy fruit. They’re a playful twist on the beloved cake, every bit as pretty as they are delicious, and destined to disappear at potlucks and family gatherings. If you’ve never tried Pineapple Upside Down Sugar Cookies before, prepare to fall in love.

Ingredients You’ll Need

You’ll be amazed at how a handful of pantry staples transforms into these joyful treats! Each ingredient brings something special to the table, from softness to brightness, and that irresistible sparkle on top.

• Unsalted Butter: Gives the cookies their rich, melt-in-your-mouth texture—make sure it’s perfectly softened for easy creaming.
• Granulated Sugar: Sweetens the cookies and adds crisp edges; a little extra for that final dusting creates dreamy caramelized tops.
• Large Egg: Provides structure and moisture, holding everything together beautifully.
• Vanilla Extract: Balances the pineapple’s tartness with warm aromatic notes—don’t skip it!
• All-Purpose Flour: The backbone of your dough, offering just the right cookie chew.
• Baking Soda: Gives the cookies lift and softness without making them cakey.
• Salt: A pinch deepens the flavors and makes every sweet bite pop.
• Canned Pineapple Rings: The star of these Pineapple Upside Down Sugar Cookies—drain and pat them dry to keep your cookies from getting soggy.
• Additional Sugar: For that essential sparkle and golden finish atop each pineapple slice.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prep Your Oven and Trays

Start by preheating your oven to 350°F (180°C). These cookies bake best on parchment-lined trays to make cleanup a breeze and guarantee easy cookie removal. This way, you’re also ensuring those delicate pineapple rings won’t stick.

Step 2: Cream Butter and Sugar

In a large mixing bowl, beat together the softened butter and granulated sugar with an electric mixer for about 2–3 minutes. You want the mixture to become light and fluffy, creating that signature sugar cookie crumb we all love.

Step 3: Add Egg and Vanilla

Crack in your egg and pour in the vanilla extract, then whip everything until it’s smooth and fully combined—the aroma at this point can only be described as heavenly.

Step 4: Mix in Dry Ingredients

In a separate bowl, whisk up your flour, baking soda, and salt. Gently add these dry goods to the wet mixture in batches, stirring just until the dough comes together soft and cohesive. Be careful not to overmix, as this keeps your Pineapple Upside Down Sugar Cookies perfectly tender.

Step 5: Scoop and Shape the Dough

Using a cookie scoop or two spoons, portion out balls of dough (about 2 tablespoons each) onto your prepared trays, leaving enough space between each for spreading—aim for two inches apart.

Step 6: Top with Pineapple Rings

Take a well-drained pineapple ring and gently press it into the top of each dough mound, flattening the ball slightly. If your rings are too large, feel free to trim or halve them so they rest comfortably atop each cookie mound. This is where the magic of Pineapple Upside Down Sugar Cookies takes shape.

Step 7: Sprinkle with Sugar

For a sparkling, caramelized finish, sprinkle a bit of granulated sugar over the exposed pineapple on each cookie. This tiny step goes a long way—the extra crunch and glossy look are irresistible.

Step 8: Bake to Golden Perfection

Slide your trays into the oven and bake for 11–13 minutes. Keep a close eye—they’re ready when the edges are lightly golden and the centers are just set. Every batch fills your kitchen with the smell of sunshine!

Step 9: Cool and Enjoy

Let your cookies cool for a few minutes on the tray before transferring to a wire rack. This helps them firm up and makes them easier to move. Once cool, indulge and savor—the sweet-tart glory is everything you hoped for in Pineapple Upside Down Sugar Cookies!

How to Serve Pineapple Upside Down Sugar Cookies

Garnishes

Top each cookie with a bright, candied cherry in the center of the pineapple ring for that classic upside-down cake look. A dusting of powdered sugar or a drizzle of simple icing can also add a playful, pretty touch that makes your cookies stand out at any gathering.

Side Dishes

For a true treat, serve your Pineapple Upside Down Sugar Cookies with scoops of vanilla ice cream or a dollop of freshly whipped cream. For something lighter, pair them with a fruit salad or even a tangy yogurt parfait—there’s no wrong answer!

Creative Ways to Present

Arrange the cookies on a platter with small tropical drink umbrellas, or stack them in glass jars for a sweet, sunny gift. Try sandwiching two cookies with a layer of coconut cream in the middle for a pineapple-coconut whoopie pie twist that everyone will rave about.

Make Ahead and Storage

Storing Leftovers

Keep any leftover Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to three days. Placing a piece of parchment between layers helps prevent sticking and keeps the pineapple rings looking picture-perfect.

Freezing

These cookies freeze beautifully! Once fully cooled, arrange them in a single layer in a freezer-safe container, using parchment between stacks. Freeze for up to two months. When you’re ready to enjoy, let them come to room temperature—perfect for a sunny treat even in the middle of winter.

Reheating

While Pineapple Upside Down Sugar Cookies are wonderful at room temp, a quick pop in a low oven (about 275°F for 2–3 minutes) will revive their just-baked warmth and bring the pineapple topping back to life. Avoid microwaving, as it can make the cookies too soft.

FAQs

Can I use fresh pineapple instead of canned?

Yes! Just slice fresh pineapple into thin rings or tidbits, and blot them dry very well. Keep in mind, canned pineapple tends to be a bit sweeter and more uniform, but fresh adds a vibrant, tangy bite if you’re up for a twist.

How do I keep my cookies from getting soggy?

The key is ensuring your pineapple is as dry as possible before placing on the dough. Pat them thoroughly with paper towels. Also, avoid storing cookies in overly humid environments, which can make the tops sticky.

Can I make these cookies gluten free?

Absolutely! Substitute the all-purpose flour with your favorite 1:1 gluten-free flour blend. Just watch the dough texture and add a tablespoon or two more flour if it looks very sticky, since pineapple adds extra moisture.

What’s the best way to cut pineapple rings for small cookies?

If your pineapple rings are too wide, simply stack them and use a small round cookie cutter, or slice them in halves or quarters to fit the dough mounds. This way, every cookie still has the perfect pop of pineapple flavor and a pretty presentation.

Can I prepare the dough in advance?

Definitely! The cookie dough can be mixed and refrigerated (well-covered) up to two days ahead of time. Let it sit at room temperature for about 20 minutes before scooping and baking so it’s easy to work with.

Final Thoughts

There’s just something special about Pineapple Upside Down Sugar Cookies—every bite is a burst of joy and sweetness. I hope you’ll give this whimsical recipe a try, share it with friends, and enjoy a little sunshine in cookie form. Happy baking!

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