Hi, I’m Sam from dishfoody.com, where comforting classics get a fresh twist. Pineapple Upside Down Sugar Cookies capture the nostalgic pineapple upside-down cake in chewy cookie form.

Buttery sugar cookie dough bakes over caramelized pineapple rings and maraschino cherries for tropical bakery perfection ready in 35 minutes.

Why This Recipe Works

Caramel magic: Brown sugar butter creates glossy pineapple glaze that doesn’t soak cookies.
Muffin tin genius: Perfect individual portions with clean upside-down release.
Sour cream tenderness: Keeps sugar cookies soft without cakiness.
Cornstarch trick: Prevents cookie spreading for defined edges.
Cherry brightness: Cuts sweetness with tangy pop in every bite.

Ingredients & Prep

Cookie Dough:
1 cup butter, softened
1½ cups granulated sugar
2 eggs
2 tsp vanilla extract
½ cup sour cream
3 cups all-purpose flour
1 tsp baking powder
1 tsp cornstarch
½ tsp salt
Topping:
13 pineapple rings (canned, drained)
13 maraschino cherries, drained
½ cup butter, melted
1 cup brown sugar, packed

Step-by-Step Instructions

Preheat oven to 350°F. Prepare mini round cake pan or muffin tin.
Cream butter and sugar until fluffy. Add eggs, vanilla, sour cream; mix smooth.
Combine dry ingredients; stir into wet just until dough forms. Set aside.
Mix melted butter and brown sugar. Spoon 1 tbsp into each cavity; spread.
Add pineapple ring + cherry in center of each.
Portion 3 tbsp cookie dough per cavity; flatten to cover fruit completely.
Bake 25 minutes until edges golden and caramel bubbles. Cool 10 minutes.
Invert onto parchment; reposition any stuck pineapple. Cool completely.

Pineapple Upside Down Sugar Cookies Recipe

Flavor Variations

Variation Key	Add/Swap	Resulting Twist
Coconut Pine	Coconut flakes + rum extract	Island escape
Banana Cherry	Banana slices + almond extract	Retro tiki
Peach Ginger	Peach slices + candied ginger	Spiced orchard
Apple Cranberry	Apple rings + dried cranberries	Fall harvest

Storage Tips

Room temp airtight 3 days; freeze 2 months. Reheat 350°F 5 minutes revives caramel shine.

FAQs

Pineapple sticks to pan? Run knife around edge; let cool longer before flipping.
Cookies too soft? Add extra cornstarch; chill dough 30 minutes pre-bake.
Caramel runny? Use more brown sugar; ensure full fruit coverage.

Conclusion

Pineapple Upside Down Sugar Cookies deliver cake nostalgia in portable bliss caramelized, chewy tropical perfection.

Pineapple Upside Down Sugar Cookies Recipe

Print Recipe

Pineapple Upside Down Sugar Cookies bake soft sugar cookie dough over caramelized pineapple rings and maraschino cherries in muffin tins, then flipped for perfect handheld cake presentation. Iconic tropical dessert reimagined as chewy cookie perfection.

Author: ssam
Prep Time: 20 mins
Cook Time: 25 mins
Total Time: 1 hr (incl cooling)
Yield: 13 cookies 1x
Category: Dessert
Method: Oven
Cuisine: American
Diet: Vegetarian

Ingredients

Scale

Sugar Cookie Dough:
1 cup unsalted butter, softened
1½ cups granulated sugar
2 large eggs
2 tsp vanilla extract
½ cup sour cream
3½ cups all-purpose flour
1 tsp baking powder
1 tsp cornstarch
½ tsp salt
Topping:
13 canned pineapple slices, drained
13 maraschino cherries, drained
½ cup unsalted butter, melted
1 cup packed light brown sugar

Instructions

1. Preheat oven to 350°F. Spray standard muffin tin generously with cooking spray.
2. Make brown sugar topping: Stir melted butter and brown sugar until smooth. Spoon 1 tbsp into each muffin cup, spreading to cover bottom.
3. Place one pineapple slice in each cup, pressing gently. Center a maraschino cherry in each pineapple hole.
4. Cream butter and sugar 2 minutes until fluffy. Add eggs, vanilla, sour cream; mix until combined. Add flour, baking powder, cornstarch, salt; mix just until dough forms.
5. Scoop 3 tbsp dough (cookie scoop #24) onto each pineapple. Gently flatten and press edges to seal. Bake 22-25 minutes until edges golden and brown sugar bubbles.
6. Cool in tin 10 minutes. Run knife around edges. Invert onto parchment-lined tray. Reposition any stuck pineapple. Cool completely.

Notes

Sour cream creates tender chewy cookie texture.
Cornstarch keeps cookies soft for days.
Generous pan spray prevents sticking.
Room temperature butter essential for proper creaming.
Store airtight 3 days room temp, 1 week refrigerated, 2 months frozen.

Nutrition

Serving Size: 1 cookie
Calories: 420
Sugar: 38g
Sodium: 220mg
Fat: 20g
Saturated Fat: 12g
Unsaturated Fat: 7g
Trans Fat: 0g
Carbohydrates: 57g
Fiber: 1g
Protein: 5g
Cholesterol: 75mg

Keywords: pineapple upside down sugar cookies, tropical cookies, pineapple cherry cookies