Oh, let me tell you about these Pineapple Upside Down Sugar Cookies! They’re this delightful twist on the classic pineapple upside-down cake, and trust me, they deliver all the nostalgia with every bite. I remember the first time I made them; the sweet aroma of buttery sugar cookies filled my kitchen, and I couldn’t resist sneaking a taste before they even cooled. The combination of the juicy pineapple with the cherry on top creates this vibrant, sunny treat that just screams happiness! They’re perfect for summer gatherings or just a cozy night in. You’re going to love how sweet and cheerful they are!

Ingredients List
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 cup brown sugar, packed
- 2 large eggs
- 2 teaspoons vanilla extract
- 3 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 can pineapple slices, drained
- 1/2 cup maraschino cherries
How to Prepare Pineapple Upside Down Sugar Cookies
Prepping the Oven and Pans
First things first, let’s get that oven going! Preheat your oven to 350°F (175°C). While that’s heating up, grab a baking sheet and give it a good spray with non-stick cooking spray or line it with parchment paper. This will ensure your delicious cookies won’t stick, making cleanup a breeze!
Creaming the Butter and Sugars
Now, in a large mixing bowl, let’s cream together the softened butter, granulated sugar, and brown sugar. I usually use an electric mixer on medium speed for about 2-3 minutes until it’s all fluffy and well combined. You want that light, airy texture that makes these cookies so scrumptious!
Adding Eggs and Vanilla
Next up, crack in those two large eggs and pour in the vanilla extract. Mix it all together until it’s just combined—don’t overdo it! You want to see a lovely creamy mixture, but a few lumps are totally okay. The smell is already heavenly, right?
Mixing Dry Ingredients
In another bowl, whisk together the all-purpose flour, baking soda, and salt. This step is super important because it helps evenly distribute the baking soda throughout the flour. Gradually add this dry mix to your wet ingredients, stirring gently until just combined. You don’t want to overmix; we’re going for soft, tender cookies here!
Arranging Pineapple and Cherries
Now for the fun part! Place your drained pineapple slices on the greased baking sheet, making sure to leave a little space between them. Pop a maraschino cherry right in the center of each pineapple slice. This not only looks adorable but adds that classic upside-down cake flair!
Adding Cookie Dough
Using a spoon or an ice cream scoop, drop cookie dough on top of each pineapple slice. Don’t worry about getting it perfect; just make sure each slice is covered. This is where the magic happens, so feel free to pile it on a bit!
Baking Instructions
Time to bake! Slide the baking sheet into your preheated oven and let those cookies bake for about 12-15 minutes. Keep an eye on them; you’ll know they’re done when they’re golden brown around the edges. The aroma wafting through your kitchen will be impossible to resist!
Cooling and Serving
Once baked, let the cookies cool on the baking sheet for about 5 minutes. Then, carefully flip them over onto a serving platter. Oh, the anticipation! You’ll want to serve these warm; trust me, they taste even better when they’re fresh out of the oven. Enjoy the sweet rewards of your hard work!
Why You’ll Love This Recipe
- They’re a delightful twist on the classic pineapple upside-down cake, bringing together the best of both worlds!
- Super easy to make with simple ingredients you probably already have in your pantry.
- Bright and colorful presentation that’s sure to impress your family and friends.
- Perfectly chewy cookies topped with juicy pineapple and a cherry, creating a burst of flavor in every bite.
- Great for any occasion, from summer picnics to cozy gatherings—everyone will be asking for the recipe!
- These cookies are quick to whip up, with minimal prep and baking time, so you can enjoy them fast!
- They store well, so you can savor them for days or share them with loved ones.
Tips for Success
- Room Temperature Ingredients: Make sure your butter and eggs are at room temperature before you start. This helps create that perfect creamy texture when mixing, which makes all the difference in your cookies!
- Don’t Skip the Chilling: If you have time, chill your cookie dough for about 30 minutes before baking. It helps the cookies hold their shape and can enhance the flavor.
- Check for Doneness: Every oven is different, so keep an eye on your cookies as they bake. They should be golden brown on the edges but still soft in the center when you pull them out. They’ll firm up as they cool!
- Use Fresh Pineapple: For an extra burst of flavor, consider using fresh pineapple instead of canned. It adds a wonderful juiciness and a more intense pineapple flavor to your cookies! Learn more about the benefits of fresh pineapple.
- Experiment with Toppings: Feel free to get creative! Try adding a sprinkle of coconut or crushed pecans on top before baking for a fun twist.
- Store Properly: To keep your cookies fresh, store them in an airtight container at room temperature. They’ll stay delicious for up to a week! You can also freeze them for longer storage—just make sure to wrap them well.
Nutritional Information
Here’s the scoop on the nutritional values for each delightful Pineapple Upside Down Sugar Cookie! Keep in mind these are estimates, but they’ll give you a good idea of what to expect:
- Serving Size: 1 cookie
- Calories: 180
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Cholesterol: 30mg
- Sodium: 90mg
- Carbohydrates: 24g
- Fiber: 1g
- Sugar: 12g
- Protein: 2g
So, as you enjoy these scrumptious cookies, you can feel a little less guilty about indulging in such a sweet treat! Perfect for sharing, but I won’t blame you if you keep them all to yourself!
FAQ Section
Can I use fresh pineapple instead of canned?
Absolutely! Using fresh pineapple will give your cookies a more intense flavor and a delightful juiciness. Just make sure to slice it into rings and drain any excess juice before using.
How do I know when my cookies are done baking?
Keep an eye on them! Your cookies are done when they’re golden brown around the edges and still slightly soft in the center. They’ll continue to firm up as they cool, so don’t worry if they seem a bit soft right out of the oven!
Can I make the dough ahead of time?
Yes! You can prepare the cookie dough and refrigerate it for up to 24 hours before baking. Just remember to let it sit at room temperature for a bit before scooping it onto the pineapple slices.
What’s the best way to store these cookies?
Store your Pineapple Upside Down Sugar Cookies in an airtight container at room temperature for up to a week. If you want to keep them longer, freeze them! Just make sure to wrap them well to prevent freezer burn.
Can I add other toppings to these cookies?
Definitely! Feel free to experiment with toppings like shredded coconut, chopped nuts, or even a drizzle of melted chocolate for an extra special treat. The possibilities are endless!
Pineapple Upside Down Sugar Cookies: 7 Sweet Bliss Bites
- Prep Time: 20 minutes
- Cook Time: 15 minutes
- Total Time: 35 minutes
- Yield: 24 cookies 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Delicious cookies with a pineapple topping that turns upside down for a sweet treat.
Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 cup brown sugar, packed
- 2 large eggs
- 2 teaspoons vanilla extract
- 3 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 can pineapple slices, drained
- 1/2 cup maraschino cherries
Instructions
- Preheat your oven to 350°F (175°C).
- Cream together butter, granulated sugar, and brown sugar.
- Add eggs and vanilla extract, mix until combined.
- In another bowl, whisk together flour, baking soda, and salt.
- Gradually add dry ingredients to wet ingredients, mixing well.
- Place pineapple slices on a greased baking sheet.
- Put a cherry in the center of each pineapple slice.
- Drop cookie dough on top of each pineapple slice.
- Bake for 12-15 minutes or until golden brown.
- Let cool for a few minutes before flipping to serve.
Notes
- Store cookies in an airtight container.
- Use fresh pineapple for a more intense flavor.
- Adjust baking time for your oven.
Nutrition
- Serving Size: 1 cookie
- Calories: 180
- Sugar: 12g
- Sodium: 90mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 24g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
Keywords: Pineapple Upside Down Sugar Cookies