You’ve perfectly captured the magic of this idea—taking a classic American dessert and reimagining it as a personal, portable treat. These cookies are indeed the perfect marriage of buttery, caramelized retro charm and modern, easy-to-share fun.
Here is your blueprint for creating these sunny, irresistible cookies.
Why These Cookies Are a Brilliant Twist
Individual Portions: Everyone gets their own perfect “cake” with a golden pineapple ring and cherry center.
Buttery Caramel in Every Bite: The brown sugar and butter topping bakes into the cookie, creating a sticky, rich glaze on top.
Stunning Presentation: They look impressive with minimal effort, making them perfect for bake sales, parties, or gifts.
The 1920s Vibe: You’re absolutely right about the history! Using canned pineapple (a revolutionary pantry staple at the time) makes this recipe accessible and authentic to its roots.
Your Ingredients
For the Caramelized Pineapple Topping (Do This First):
1 (20 oz) can pineapple rings in juice (you’ll need 10-12 rings)
10-12 maraschino cherries
⅓ cup (5 ⅓ tbsp / 75g) unsalted butter
⅔ cup (135g) packed light brown sugar
1 teaspoon vanilla extract
For the Tender Sugar Cookie Base:
2 ¾ cups (344g) all-purpose flour, spooned & leveled
1 teaspoon baking soda
½ teaspoon baking powder
½ teaspoon salt
1 cup (2 sticks / 226g) unsalted butter, softened to room temperature
1 ½ cups (300g) granulated sugar
1 large egg, room temperature
2 teaspoons vanilla extract
⅓ cup (80g) sour cream (the secret to a soft, cake-like crumb)
The Foolproof Method: A Two-Step Process
Step 1: Prepare the Pans & Topping
Preheat oven to 350°F (175°C). Generously grease the cups of two standard muffin tins.
Make the Caramel Glaze: In a small saucepan, melt ⅓ cup butter with the brown sugar over medium heat. Stir until smooth and bubbly. Remove from heat and stir in 1 tsp vanilla. Set aside.
Pat your pineapple rings VERY dry with paper towels. This is crucial to prevent a soggy cookie bottom.
Place 1 teaspoon of the caramel glaze in the bottom of each muffin cup. Place one dried pineapple ring over the glaze. Place one cherry in the center of each ring.
Step 2: Make the Cookie Dough & Assemble
Whisk together the flour, baking soda, baking powder, and salt in a medium bowl.
In a large bowl, beat the softened butter and granulated sugar until light and fluffy (3 mins). Beat in the egg and vanilla.
Mix in half of the dry ingredients, then all of the sour cream, then the remaining dry ingredients. The dough will be thick and soft.
Assemble: Using a large cookie scoop or spoon, place a ball of dough (about 2-3 tablespoons) directly on top of each pineapple ring in the muffin cups. Gently spread the dough to the edges to seal in the pineapple.
Step 3: Bake, Cool & The Grand Flip
Bake for 15-18 minutes, until the cookie tops are lightly golden and set.
IMPORTANT: Let the pans cool on a wire rack for only 5 minutes. While still warm, run a knife around each cookie. Place a large baking sheet or piece of parchment over the muffin tin and carefully but confidently flip it over. Gently lift the muffin tin away. If any glaze sticks, you can scrape it out and spoon it back onto the cookies.
🍍 Pro Baker’s Secrets for Perfection
Dry the Pineapple: This is the most important step. Wet pineapple will steam and make the cookie bottom soggy.
Use Room Temp Ingredients: This ensures the cookie dough emulsifies properly for an even, tender texture.
Don’t Over-Bake: The cookies will continue to set as they cool. They are done when the edges are just golden.
The Flip Timing: If you wait too long, the caramel will harden and stick. If you flip too soon, it can be messy. The 5-minute window is perfect.
📋 FAQ & Troubleshooting
Can I use fresh pineapple? Yes, but it must be cored, sliced into rings, and cooked (simmered in a little water for 5-10 mins) to soften first.
My caramel stuck to the pan! No worries—just scrape it out while warm and spoon it back onto the cookies. Next time, ensure your pan is very well-greased.
Can I make these in advance? They are best served the same day. Store leftovers in a single layer in an airtight container.
Conclusion: Your New Signature Sunshine Cookie
These cookies are a guaranteed showstopper. They bring the joy of a classic dessert into a form that’s perfect for sharing and gifting. By mastering the simple flip, you deliver a beautiful, delicious treat that tastes like a ray of sunshine.
So, dry that pineapple, make that caramel, and get ready for the applause. Your journey to becoming the baker with the most nostalgic and delicious cookie recipe starts now.