Imagine your classic sugar cookie—tender, buttery, and rolled in sparkly sugar—but with a surprise bite of golden, pineapple-infused caramel right in the center. These Pineapple Upside-Down Sugar Cookies are a playful mashup of two beloved desserts: the nostalgic charm of a melt-in-your-mouth sugar cookie and the tropical flair of a pineapple upside-down cake.
The secret? A spoonful of canned pineapple ring filling tucked into each cookie before baking, where it melts into a gooey, caramelized center that echoes the magic of that classic stovetop cake—minus the skillet and the flip. They’re soft, chewy, golden-edged, and finished with turbinado sugar for a subtle crunch.
Perfect for holiday cookie trays, summer parties, or anytime you want a little sunshine in your bite.
Why You’ll Love These Cookies
🍍 Tropical twist on a classic—nostalgic with a fun surprise
🧈 Soft, chewy texture with a buttery crumb
🌟 No fancy tools—one bowl, 20 minutes active time
🥣 Uses pantry staples + one can of pineapple
☀️ Bright, cheerful, and always a conversation starter
If you love cookies that are familiar yet inventive, this is your new seasonal favorite.¾ cup (1½ sticks / 170g) unsalted butter, softened
¾ cup (150g) granulated sugar
1 large egg, room temperature
1 tsp pure vanilla extract
2 cups (250g) all-purpose flour
½ tsp baking soda
¼ tsp salt
¼ tsp ground cinnamon (optional—adds warmth)
For the Filling & Topping:
1 (20 oz) can pineapple rings in juice, well-drained
2 tbsp brown sugar
¼ tsp ground ginger or nutmeg (optional)
Turbinado or coarse sugar for rolling
💡 Pro Tips:
Drain pineapple VERY well—pat dry with paper towels to avoid soggy cookies.
Chop filling finely—you want a jam-like texture, not big chunks.
Chill dough 15 mins if too soft (helps hold shape during baking).
