Ingredients

Topping

• ¼ cup (55 g) unsalted butter, melted
• ½ cup (100 g) light brown sugar, packed
• 12 pineapple rings, halved (or 24 tidbits/chunks), well drained
• 24 maraschino cherries, well drained

Sugar Cookie Dough

• 1 cup (226 g) unsalted butter, softened
• 1 cup (200 g) granulated sugar
• 1 large egg
• 1 tsp vanilla extract
• 2¼ cups (280 g) all-purpose flour
• ½ tsp baking powder
• ¼ tsp baking soda
• ½ tsp fine salt

Shortcut: Swap the homemade dough for one 17–18 oz (480–510 g) roll of refrigerated sugar-cookie dough.

Instructions

1. Prep pans: Heat oven to 350°F / 175°C. Lightly grease a 24-cup mini muffin pan (or standard muffin tin for larger cookies).
2. Topping: Mix melted butter and brown sugar. Spoon 1 tsp into each mini cup (2–3 tsp for standard). Place a cherry in the center and tuck in a piece of pineapple so the fruit sits flat.
3. Dough: Beat butter and sugar until light and fluffy (2–3 min). Beat in egg and vanilla. Whisk flour, baking powder, baking soda and salt; add to bowl and mix just until combined.
4. Portion: Roll dough into balls—about 1 Tbsp (18–20 g) for mini, 2 Tbsp (35–40 g) for standard. Set over the fruit and gently flatten to cover.
5. Bake: Mini for 10–12 min (standard 13–15) until edges turn golden and centers look set.
6. Invert: Rest 5 minutes. Loosen edges with a thin knife. Invert pan onto a tray to release; replace any fruit that sticks. Cool on a rack.

Tips & Variations

• Drain well: Pat pineapple and cherries dry so the topping stays glossy.
• Coconut twist: Add ¼ cup fine shredded coconut to the topping or ½ tsp coconut extract to the dough.
• Cinnamon hint: Mix a pinch of cinnamon into the brown sugar.
• Storage: Best the day made. Keep covered at room temp 1 day or refrigerate up to 3 days; warm 10–15 sec to refresh.
• Freeze: Freeze baked, cooled cookies up to 2 months; thaw uncovered so tops stay shiny.