Step-by-Step Instructions
1. Preheat the Oven
Set oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
2. Cream the Butter & Sugar
In a large bowl, beat butter and sugar together until light and fluffy (2–3 minutes).
3. Add Wet Ingredients
Mix in the egg and vanilla extract until smooth.
4. Combine Dry Ingredients
In a separate bowl, whisk flour, baking powder, and salt. Gradually add to wet ingredients, mixing until just combined. Chill dough for 20 minutes if it feels too soft.
5. Shape the Cookies
Scoop tablespoon-sized dough balls onto the baking sheet, spaced 2 inches apart. Press a small indentation in each with your thumb or spoon.
6. Add the Tropical Toppings
-
Spoon ½ tsp crushed pineapple into each indentation.
-
Gently press a halved maraschino cherry in the center.
7. Bake
Bake for 10–12 minutes, until edges are set and lightly golden. Cool on the sheet for 5 minutes, then transfer to a wire rack.
Tips for the Best Cookies
-
Drain pineapple really well – excess juice can make cookies soggy.
-
Use room temperature ingredients for smooth mixing.
-
Don’t overmix the dough – once flour is in, stop when just combined.
-
Chill the dough if it feels sticky; this helps cookies hold shape.
Creative Variations
-
Add toasted coconut flakes for extra crunch.
-
Swap cherries for strawberries or dried cranberries.
-
Mix lime zest into the dough for citrus brightness.
-
Make cookie bars by pressing dough into a 9×9-inch pan and topping with pineapple + cherries.
Serving & Storage
Pair With: Herbal tea, lemonade, or iced coffee for a refreshing match.
Storage:
-
Airtight container at room temperature: up to 3 days
-
Fridge: up to 1 week
-
Freezer: up to 2 months (layer with parchment between cookies)
FAQs
Q: Can I use fresh pineapple instead of canned?
Yes—just finely chop and press out as much liquid as possible.
Q: Can I make the dough ahead of time?
Absolutely! Chill for up to 2 days or freeze dough balls, then thaw slightly before baking.
Q: Do I have to use cherries?
Nope! Try blueberries, raspberries, or even chocolate chips for a fun twist.
Nutrition (per cookie, ~24 cookies)
-
Calories: ~150
-
Carbs: 18g
-
Fat: 8g
-
Protein: 2g
Final Thought
These Pineapple Upside Sugar Cookies are little edible bursts of sunshine—bright, tropical, and nostalgic all at once. They bring the spirit of pineapple upside-down cake into bite-sized form, and I promise they’ll steal the spotlight at any gathering.
