Pineapple Upside Sugar Cookies

As seen in Classic American Comfort Dishes.

This treat combines a buttery, soft cookie dough base with a vibrant pineapple ring atop each disk. Butter and sugar are creamed until pale and fluffy, eggs and vanilla blended in, followed by gradual mixing of dry flour, baking soda, and salt. The dough is scooped into disks, each crowned with a carefully pressed pineapple ring and sprinkled sugar to create a caramelized finish as it gently bakes. Cooling on the tray ensures the cookies set perfectly before moving to a rack. The final bite reveals a tender cookie layered with sweet, tangy fruit and a sugary sparkle.

Breanna
Created By Breanna
Last updated on Sat, 16 Aug 2025 14:42:59 GMT
A stack of pineapple slices with sugar on top. Save Pin
A stack of pineapple slices with sugar on top. | gracefulflavors.com

The scent of sweet pineapple mingled with buttery sugar always brings me right back to summer afternoons spent baking with my mom. This cookie was born one day when we had a spare can of pineapple rings on the counter and a craving for something a little different. Watching those golden rings slowly caramelize on soft, buttery cookies felt like catching a small bit of sunshine in every bite.

I first stumbled on this combo years ago at a backyard gathering. Someone had brought pineapple upside-down cake cookies, and the way that tangy pineapple punch paired with the buttery dough blew me away. It sparked me to create my own version with a fuss-free cookie dough that highlights the topping without overwhelming it.

Essential Ingredients

  • Unsalted butter: the backbone of luscious texture; aim for room temperature to cream properly
  • Granulated sugar: provides sweetness and caramelizes beautifully on top
  • Egg: binds everything together and adds richness; large eggs work best
  • Vanilla extract: lends warmth and depth; choose a pure extract for natural flavor
  • All-purpose flour: the sturdy base of the dough; sift to avoid lumps
  • Baking soda: helps the cookies rise just enough for a tender crumb
  • Salt: balances sweetness and enhances other flavors; fine salt blends evenly
  • Canned pineapple rings: the star of the show; make sure to drain and pat dry completely to prevent soggy cookies
  • Extra granulated sugar: sprinkled on pineapple for caramelized sparkle during baking

When shopping, pick pineapple rings that are uniform in size and free from bruises or syrup residue. Using room temperature butter is a small step that makes a big difference for creaming.

Cooking Process

Building the Base:
Cream the softened butter with sugar until light and fluffy; this incorporates air, giving cookies their tender texture.
Binding the Ingredients:
Beat in egg and vanilla until smooth; they tie the dough together and bring depth to the flavor.
Dry Elements Meet Wet:
Whisk flour, baking soda, and salt separately before adding gradually to avoid overmixing, which can toughen cookies.
Rolling and Spacing:
Form dough balls of consistent size and flatten gently; this ensures even baking and helps pineapple rings stay in place.
Top Dressings:
Place each pineapple ring on dough, pressing lightly so they don’t slip during baking. Sprinkle sugar on top to create that signature caramelized crunch.
Golden Finish:
Bake at moderate heat allowing the edges to turn golden while the center remains soft, capturing the perfect balance of texture.
Cooling Off:
Let cookies set briefly on the pan before moving to a rack; this helps the pineapple adhere and preserves the cookie’s shape.
A stack of pineapple rings with sugar on top. Save Pin
A stack of pineapple rings with sugar on top. | foodiffy.com

Recipe Highlights

  • Soft yet crisp cookies enriched with juicy, caramelized pineapple
  • A refreshing, fruity twist on classic sugar cookies, offering a hint of tropical sweetness
  • Simple ingredients perfect for pantry staples or quick weeknight treats

Once, in my excitement, I added pineapple rings that weren’t dried thoroughly and ended up with a sticky, spread-out mess—but that taught me the difference drying makes in keeping shape and texture. Now I’m meticulous about patting dry those golden circles.

Make-Ahead Strategies

Prepare the dough in advance and refrigerate it for up to 2 days. When ready, roll, top, and bake fresh to preserve pineapple’s bright flavor and cookie’s tender texture. Dough also freezes well for up to 3 months; thaw overnight in the fridge before rolling.

Flavor Variations

Try a sprinkle of cinnamon or nutmeg in the dough for a warm spice note that complements the pineapple. For extra zing, add a teaspoon of finely grated lime zest to the butter and sugar mixture. Swap canned pineapple for fresh rings when in season for a vibrant, juicy upgrade.

Kitchen Tool Recommendations

A good quality electric mixer makes creaming butter and sugar effortless. Silicone spatulas help scrape down the bowl without wasting dough. Use parchment paper-lined baking sheets to prevent sticking and make cleanup a breeze.

Cooking Secrets

  • Always drain and thoroughly pat dry pineapple rings; moisture can flatten cookies and prevent caramelization.
  • Don’t overmix once dry ingredients are added; too much mixing develops gluten, leading to tough cookies.
  • Sprinkle sugar over pineapple just before baking for that irresistible crunch and golden glaze.
A stack of sliced pineapple. Save Pin
A stack of sliced pineapple. | foodiffy.com

Common Questions

→ How do I prevent the pineapple rings from making cookies soggy?

Make sure to drain the pineapple rings thoroughly and pat them completely dry before placing on the dough. This helps avoid excess moisture during baking.

→ What is the best way to achieve a caramelized sugar topping?

After pressing the pineapple ring onto each cookie dough disk, sprinkle a little granulated sugar on top before baking. This melts and caramelizes for a sparkly, crisp finish.

→ Can I use fresh pineapple instead of canned?

Fresh pineapple can work if it's well-drained and patted dry, but canned rings are preferred for consistent sweetness and texture.

→ Why is it important not to overmix the dough?

Mixing just until combined keeps the cookies tender and soft, avoiding tough texture caused by developing too much gluten.

→ How long should the cookies cool before handling?

Allow the cookies to cool on the baking sheet for around 5 minutes to set, then transfer to a wire rack to cool completely for best texture.

Pineapple Upside Sugar Cookies

Sweet cookies with a pineapple ring topping and a delicate sugar crunch.

Preparation Time
15 Minutes
Cooking Time
14 Minutes
Overall Time
29 Minutes
Created By: Breanna

Type: Comfort Food

Skill Level: Simple

Regional Origin: American

Recipe Output: 24 Portions (Approximately 24 cookies)

Diet Preferences: Meat-Free

What You'll Need

→ Cookie Dough Base

01 1 cup unsalted butter, softened to room temperature
02 1 cup granulated sugar
03 1 large egg
04 1 teaspoon vanilla extract

→ Dry Ingredients

05 2 1/2 cups all-purpose flour
06 1/2 teaspoon baking soda
07 1/4 teaspoon salt

→ Pineapple Topping

08 10 to 12 canned pineapple rings, well-drained and patted completely dry
09 Extra granulated sugar for sprinkling

How to Make It

Step 01

Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.

Step 02

In a large bowl, beat softened butter and granulated sugar with an electric mixer until light, fluffy, and pale, approximately 3 to 4 minutes.

Step 03

Add egg and vanilla extract to the butter mixture, beating until fully combined and smooth.

Step 04

In a separate bowl, whisk together all-purpose flour, baking soda, and salt.

Step 05

Gradually add dry ingredients to wet ingredients, mixing just until a soft dough forms. Avoid overmixing.

Step 06

Roll dough into balls using approximately 1 1/2 tablespoons per cookie, place on prepared sheets, and gently flatten each into a disk, leaving sufficient space between.

Step 07

Press one pineapple ring gently onto each dough disk to secure it for baking.

Step 08

Sprinkle extra sugar over pineapple rings and bake cookies for 12 to 14 minutes until edges turn golden and cookies are set.

Step 09

Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely before serving or storing.

Additional Tips

  1. Ensure pineapple rings are thoroughly dried to prevent excess moisture from softening the cookies.

Must-Have Tools

  • Electric mixer
  • Parchment paper
  • Wire cooling rack

Allergy Details

Double-check all ingredients for allergens and consult a professional if unsure.
  • Contains egg and gluten.