Crispy Pineapple Upside Down Sugar Cookies
Crispy Pineapple Upside Down Sugar Cookies that delight every bite. After making these many times, I’ve discovered the trick to a perfect, golden crust. Jump to the recipe or keep reading for my best tips. If you love recipes like this, you’ll also enjoy Easy Sloppy Joe Potato Skillet and Crispy Blueberry Cake Donuts.
Why This Crispy Pineapple Upside Down Sugar Cookies Is Pure Comfort
- Crispy edges and soft centers
- Warm, gooey pineapple topping
- Easy and quick to make
- Better than takeout
What You'll Need for Crispy Pineapple Upside Down Sugar Cookies
Choosing the right ingredients makes a big difference, but this recipe is forgiving enough to work with what you have.
- 1 can pineapple slices
- 1 box sugar cookie mix
- 1/2 cup butter
- 1/4 cup brown sugar
- 1 tsp vanilla extract
- 1/2 tsp cinnamon
- Optional: Maraschino cherries
📝 Ingredient Notes
- Butter: Melted
- Pineapple slices: Reserve juice for topping
🛒 Tools & Equipment I Recommend
- Non-stick baking sheet — Prevents cookies from sticking → See on Amazon
- Silicone baking mat — Ensures even baking → See on Amazon
How to Make Crispy Pineapple Upside Down Sugar Cookies
- Preheat oven: Preheat oven to 375°F (190°C).
- Prepare pan: Melt butter and mix with brown sugar. Pour into greased 12-cup muffin tin. Top with pineapple slices and cherries.
- Prepare dough: Mix cookie dough according to package instructions. Add vanilla and cinnamon.
- Bake: Drop dough onto pineapple slices. Bake for 12-14 minutes or until edges are golden.
- Invert: Let cool for 5 minutes. Invert onto a plate. Drizzle with reserved pineapple juice.
Cook's Tips for Perfect Crispy Pineapple Upside Down Sugar Cookies
- Common mistake and fix: Don't overbake. Check cookies at 12 minutes to prevent dry edges.
- Tip: For easier removal, grease muffin tin with cooking spray.
- Tip: Use a spoon to gently press dough onto pineapple slices for even baking.
Storing & Reheating Crispy Pineapple Upside Down Sugar Cookies
Short-Term Storage
Store in an airtight container in the fridge. Store leftovers in an airtight container at room temperature for up to 5 days. Make-ahead tip: Prepare dough ahead of time and store in the fridge. Bake as directed.
Freezing Crispy Pineapple Upside Down Sugar Cookies
Not recommended for freezing.
How to Reheat Without Drying It Out
Oven: Reheat in a 350°F (175°C) oven for 5-7 minutes. Microwave: Not recommended for reheating.
Recipe Notes
- Chef tip: For a tangier topping, use pineapple juice instead of water in the cookie dough.
- Best substitution: Substitute canned mandarin oranges for pineapple.
- Make-ahead: Prepare dough ahead of time and store in the fridge. Bake as directed.
- Scaling: This recipe can be doubled for a larger batch.
- Troubleshooting: If cookies are sticking, use a spoon to gently loosen them before inverting.
Want to level up this recipe?
Pineapple corer and slicer — Makes prep work faster and easier → Check price on Amazon
Crispy Pineapple Upside Down Sugar Cookies
Ingredients
Main Ingredients
- 1 can pineapple slices
- 1 box sugar cookie mix
- 1/2 cup butter
- 1/4 cup brown sugar
Seasonings
- 1 tsp vanilla extract
- 1/2 tsp cinnamon
Optional Toppings
- Maraschino cherries
Instructions
- Preheat oven: Preheat oven to 375°F (190°C).
- Prepare pan: Melt butter and mix with brown sugar. Pour into greased 12-cup muffin tin. Top with pineapple slices and cherries.
- Prepare dough: Mix cookie dough according to package instructions. Add vanilla and cinnamon.
- Bake: Drop dough onto pineapple slices. Bake for 12-14 minutes or until edges are golden.
- Invert: Let cool for 5 minutes. Invert onto a plate. Drizzle with reserved pineapple juice.
Notes
- Chef tip: For a tangier topping, use pineapple juice instead of water in the cookie dough.
- Best substitution: Substitute canned mandarin oranges for pineapple.
- Make-ahead: Prepare dough ahead of time and store in the fridge. Bake as directed.
- Scaling: This recipe can be doubled for a larger batch.
- Troubleshooting: If cookies are sticking, use a spoon to gently loosen them before inverting.
Storage
- Fridge: Store leftovers in an airtight container at room temperature for up to 5 days.
- Freezer: Not recommended for freezing.
- Oven reheat: Reheat in a 350°F (175°C) oven for 5-7 minutes.
- Microwave reheat: Not recommended for reheating.
- Make ahead: Prepare dough ahead of time and store in the fridge. Bake as directed.
Nutrition Per Serving
- Calories: 130
- Protein: 1g
- Fat: 6g
- Carbs: 18g
- Fiber: 0.5g
- Sugar: 12g
- Sodium: 120mg
- Cholesterol: 15mg
- Sat. Fat: 3.5g
Nutritional values are estimates only. Actual values may vary by brand and portion size.
Crispy Pineapple Upside Down Sugar Cookies FAQs
Prepare dough ahead of time and store in the fridge. Bake as directed.
Cookies were overbaked. Check at 12 minutes and remove when edges are golden.
Yes, but the texture and consistency may vary. Use 1 cup of diced fresh pineapple and adjust liquid as needed.
No, this recipe is not suitable for the air fryer.
Substitute canned mandarin oranges for pineapple.
A Warm Final Note
I can’t wait for you to try Crispy Pineapple Upside Down Sugar Cookies and see how effortlessly it comes together. When you make it, pop back here and leave a rating or share how it turned out — I love hearing from you!
