- ½ cup (1 stick / 115g) unsalted butter, softened
- ¾ cup (150g) granulated sugar
- 1 large egg, room temperature
- 1 tsp pure vanilla extract
- 1½ cups (190g) all-purpose flour
- 1½ tsp baking powder
- ¼ tsp salt
- ¼ cup (60ml) milk
For the Pineapple Topping (Bottom):
- 2 tbsp unsalted butter, melted
- ¼ cup (50g) packed brown sugar
- ½ cup (80g) crushed pineapple, well-drained
- 18–24 maraschino cherry halves (plus extra for centers)
💡 Pro Tips:
- Drain pineapple thoroughly—excess liquid makes cookies soggy.
- Use room-temperature egg—ensures even mixing.
- Line muffin tin with paper liners—makes removal easy.
Step-by-Step Instructions (Fruity, Tender, Foolproof)
1. Prep the Topping
- Preheat oven to 350°F (175°C). Line a muffin tin with paper liners (not a cookie sheet!).
- In each liner, place:
- ½ tsp melted butter
- ½ tsp brown sugar
- 1 tsp drained crushed pineapple
- 1 cherry half (press into center)
2. Make the Dough
- Beat butter and granulated sugar until light and fluffy (2–3 mins).
- Add egg and vanilla; beat until smooth.
- Whisk flour, baking powder, and salt in a bowl.
- Alternately add dry ingredients and milk to wet mixture, starting and ending with flour. Mix until just combined.
3. Fill the Tin
- Spoon dough over pineapple-cherry base in each liner, filling ¾ full.
- Optional: Press an extra cherry half into the center of each.
4. Bake to Perfection
- Bake 18–22 minutes, until edges are golden and centers spring back.
- Cool 5 minutes in pan, then carefully invert onto a wire rack (like a true upside-down cake!).
- Optional: Drizzle with vanilla glaze (1 cup powdered sugar + 2 tbsp milk).
Serving Suggestions
- ☕ Classic: With coffee or iced tea
- 🥥 Tropical twist: Sprinkle with toasted coconut
- 🍦 Decadent: Serve warm with vanilla ice cream
- 🎁 Gift idea: Package in cellophane bags with ribbon
Make-Ahead & Storage Tips
- Room temperature: Keeps in airtight container up to 3 days.
- Fridge: Up to 5 days—great for meal prep.
- Freeze: Unfrosted cookies freeze well up to 2 months. Thaw at room temp.
Frequently Asked Questions
Q: Gluten-free?
A: Yes! Use a 1:1 GF flour blend (like Bob’s Red Mill).
Q: Can I use fresh pineapple?
A: Yes—but chop finely and drain well to avoid excess moisture.
Q: Why a muffin tin?
A: It creates the perfect “upside-down” shape and contains the juicy topping.
Q: Too cakey?
A: That’s the point! These are meant to be soft and tender—not crisp like traditional sugar cookies.
❤️ The Heart of the Cookie
Pineapple Upside-Down Sugar Cookies aren’t just dessert—they’re a playful homage to retro baking. They’re what you make when you want to surprise guests, brighten a gray day, or simply enjoy a bite of tropical nostalgia.
So drain that pineapple, line that tin, and bake with joy. Because the best cookies aren’t always classic—they’re fruity, fun, and made with love.
“Good cookies don’t need a bakery—they just need pineapple, cherries, and someone hungry.” 🍍✨