Pineapple Upside Down Sugar Cookies
Bright, nostalgic cookies that combine caramelized pineapple flavor with soft sugar cookie dough, perfect for potlucks and sunny snacks.
Ingredients
Cookie dough ingredients
- 2.5 cups all-purpose flour (or 1:1 gluten-free blend)
- 0.5 tsp baking powder
- 0.25 tsp baking soda
- 0.5 tsp fine sea salt
- 1 cup (2 sticks) unsalted butter, room temp (or dairy-free stick for veg variant)
- 1 cup granulated sugar (or coconut sugar for a slightly more wholesome vibe)
- 1 large egg room temp
- 1 large egg yolk room temp
- 1 tsp vanilla extract (pure)
- 0.75 cup crushed canned pineapple, drained well (or finely chopped fresh pineapple) this is the STAR
- 0.33 cup light brown sugar for caramelized top
- 2 tbsp cornstarch for a tender cookie
- Maraschino cherries or glace cherries, halved for garnish (optional)
Instructions
Make the caramelized pineapple topping
- Mix the drained crushed pineapple with the light brown sugar until sticky and glossy. Press a spoonful onto the bottom of a lined baking sheet or a mini muffin tin for cookie-cup shapes.
Whip the dough
- Beat the butter and granulated sugar until lighter and fluffy, add the egg, yolk, and vanilla, then fold in the dry mix with cornstarch. The dough should be soft and slightly tacky.
Assemble
- Scoop dough into rounded tablespoon balls and press gently onto the pineapple caramel, smoothing edges. Top with a cherry half if desired.
Bake & cool
- Bake until edges are set and bottoms are golden, about 10–12 minutes. Cool completely on the pan for 15–20 minutes before flipping or lifting carefully.
Notes
Make ahead: dough freezes well, baked cookies keep in an airtight container for up to 4 days, and can be frozen as singles. Reheat in a 300°F oven for 5-7 minutes or microwave for 8-10 seconds. For lower sugar, reduce granulated sugar by 2–3 tbsp.