Introduction
Imagine the caramelized sweetness of pineapple upside-down cake transformed into a buttery, bite-sized cookie. These Pineapple Upside-Down Sugar Cookiescombine the nostalgic flavors of the classic dessert with the convenience of cookies—perfect for picnics, bake sales, or a sunny afternoon treat. Each cookie features a golden caramelized pineapple top and a soft, vanilla-scented base, delivering tropical vibes in every bite.
Culinary Techniques & Science
- Caramelization: Cooking pineapple in brown sugar creates deep, rich flavor.
- Cookie Texture: Creaming butter and sugar incorporates air for a tender crumb.
- Moisture Control: Patting pineapple dry prevents soggy cookies.
- Even Baking: Chilling the dough prevents excessive spreading.
Ingredients & Substitutions
Makes 24 cookies
For the Pineapple Topping:
- 1 cup fresh pineapple, finely diced (or canned, drained well)
- ¼ cup light brown sugar (or coconut sugar)
- 1 tbsp unsalted butter
- ½ tsp vanilla extract
For the Cookie Dough:
- 2 ¼ cups all-purpose flour (or gluten-free 1:1 blend)
- ½ tsp baking powder
- ¼ tsp salt
- ¾ cup unsalted butter, softened (or vegan butter)
- ¾ cup granulated sugar
- 1 large egg (or flax egg: 1 tbsp ground flax + 3 tbsp water)
- 2 tsp vanilla extract
- Maraschino cherries, halved(optional, for decoration)
Step-by-Step Instructions
1. Prepare the Pineapple Topping
- In a skillet over medium heat, melt butter and brown sugar.
- Add pineapple and cook for 5–7 minutes until caramelized.
- Stir in vanilla, then spread on parchment paper to cool.
Pro Tip: Blot pineapple with a paper towel to remove excess moisture.
2. Make the Cookie Dough
- Whisk together flour, baking powder, and salt in a bowl.
- In a separate bowl, cream butter and sugar until fluffy (~3 mins).
- Beat in egg and vanilla.
- Gradually mix in dry ingredients until just combined.
- Fold in ½ cup cooled pineapple(reserve rest for topping).
Pro Tip: Chill dough 30 mins for easier handling.
3. Assemble & Bake
- Preheat oven to 350°F (175°C). Line baking sheets with parchment.
- Scoop 1½ tbsp dough per cookie; place 2″ apart.
- Press 1–2 pineapple pieces and a cherry half onto each.
- Bake 10–12 minutes until edges are golden.
- Let cool 5 minutes on the sheet, then transfer to a rack.
Pro Tips for Success
- ✔ Uniform size: Use a cookie scoop for even baking.
- ✔ Prevent sticking: Grease parchment paper lightly.
- ✔ Extra caramel flavor: Brush cookies with reserved pineapple syrup after baking.
Troubleshooting
- Too flat? Dough may be too warm—chill longer.
- Pineapple sliding off? Press pieces gently into dough before baking.
- Dry cookies? Reduce bake time by 1–2 minutes.
Creative Variations
Coconut Lime
Add ½ cup shredded coconut + 1 tbsp lime zest to dough.
Spiced Rum
Soak pineapple in 1 tbsp rum before cooking.
Mini Skillets
Bake in cast-iron pans for individual desserts.
Serving Suggestions
- Warm with vanilla ice cream for à la mode cookies.
- Drizzled with caramel sauce for extra decadence.
- Packaged in cellophane bags for edible gifts.
Conclusion
These Pineapple Upside-Down Sugar Cookies are a sunshine-filled twist on two beloved classics. With their sticky-sweet tops and chewy centers, they’re guaranteed to transport you to the tropics. Easy enough for beginners yet impressive for any occasion, this recipe is your ticket to cookie stardom.
