HomePineapple Upside Down Sugar Cookies: The Two-Bite Vacation That Will Blow Your Mind
Pineapple Upside Down Sugar Cookies: The Two-Bite Vacation That Will Blow Your Mind
Forget the cake. We’re taking the iconic, caramelized flavors of a classic pineapple upside down cake and transforming them into the ultimate portable, shareable, irresistible cookie. Pineapple Upside Down Sugar Cookies are the genius mashup you never knew you needed: a soft, buttery sugar cookie base topped with a sweet, jewel-like ring of caramelized pineapple and a maraschino cherry, baked until the fruit sinks into a sticky, golden glaze.
Imagine the buttery crunch of a perfect sugar cookie meeting the gooey, tropical sweetness of baked pineapple and cherry in every single bite. This isn’t just a cookie; it’s a two-bite vacation to a tropical paradise and a stunning showstopper that will disappear from any cookie tray in seconds. Get ready to redefine what a cookie can be.
(Strategic Ad Placement – Recommended here: Leaderboard or Anchor Ad)
Why This Mashup is a Culinary Masterstroke
This recipe brilliantly solves the one problem of pineapple upside down cake: it’s a whole cake. By portioning the magic into cookies, you get maximum caramelized edge in every bite and the perfect individual serving. The sugar cookie dough is sturdy enough to hold the juicy topping without getting soggy, baking up with a slightly crisp edge and a tender center that soaks up the pineapple glaze. They’re visually stunning, fun to eat, and deliver that iconic flavor in a whole new format.
Your Blueprint for Tropical Cookie Bliss
Part 1: The Buttery, Sturdy Sugar Cookie Base
All-Purpose Flour (2 ½ cups): The structure.
Cornstarch (2 tsp): The secret to an ultra-soft, melt-in-your-mouth texture.
Baking Soda & Cream of Tartar: For the perfect rise and slight tang.Unsalted Butter (1 cup, softened): For rich flavor.
Granulated Sugar (1 cup) & Brown Sugar (½ cup): For sweetness, moisture, and a hint of caramel flavor.
Egg (1 large) & Egg Yolk (1): The extra yolk guarantees richness and tenderness.
Vanilla Extract (2 tsp): The aromatic soul.
Part 2: The Caramelized Pineapple Topping
Canned Pineapple Rings (1 can, 20 oz): In 100% juice, drained and patted very dry. Cut each ring into 6-8 small wedges.
Maraschino Cherries (1 jar): Halved or quartered.
Unsalted Butter (6 tbsp), melted: For the caramel glaze.
Brown Sugar (¾ cup, packed): Creates the signature sticky, caramelized layer.
A Pinch of Salt: To balance the extreme sweetness.
(Strategic Ad Placement – Recommended here: In-Article Rectangle)
Step-by-Step: Creating Your Edible Jewels
Step 1: Make the Caramel Topping & Prep Fruit
Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper.
In a small bowl, mix the melted butter, brown sugar, and salt until it forms a thick, spreadable paste.
Drain pineapple rings thoroughly and pat them dry with paper towels. Cut into small wedges. Pat cherries dry and halve them.
Step 2: Create the Sugar Cookie Dough
In a medium bowl, whisk flour, cornstarch, baking soda, cream of tartar, and salt. Set aside.
In a large bowl, cream softened butter, granulated sugar, and brown sugar until light and fluffy (3-4 mins). Beat in the egg, egg yolk, and vanilla until smooth.
Gradually add the dry ingredients to the wet, mixing on low until just combined. The dough will be thick and soft.
Step 3: The Artistic Assembly
Scoop dough into 1.5-inch balls (about 2 tbsp each). Place them 3 inches apart on the prepared baking sheets. They will spread.
Press your thumb into the center of each dough ball to create a wide, deep well.
Place 1-2 small wedges of dried pineapple and a piece of cherry into each well.
Using a small spoon, carefully place about ½ tsp of the brown sugar-butter paste directly on top of the fruit in each well.
For Complete Cooking STEPS Please Head On Over To Next Page Or Open button (>) and don’t forget to SHARE with your Facebook friends.
