Pineapple upside down cookies

Oh, friends, I’m so excited to share this recipe with you today. You know those classic pineapple upside down cakes? The ones with the gooey, caramelized pineapple on top and that unbelievably moist cake underneath? Well, imagine all that glorious flavor, all that comforting sweetness, shrunk down into the most delightful little cookies. That’s exactly what these pineapple upside down cookies are! My mom used to make the cake for my birthday every year, and honestly, the smell of it baking would fill the entire house with such a cozy, happy vibe. When I first dreamt up these cookies, I was craving that exact same feeling, but maybe something a little more… snackable. Something I could just grab with my morning coffee or share with neighbors on a whim. And let me tell you, these little gems absolutely nail it. They’re not just cookies; they’re little bursts of sunshine, pure joy in every bite, and they’ve quickly become a staple in my baking rotation. If you love that classic pineapple upside down cake flavor, but want something a bit quicker and just as utterly delicious, you are going to be obsessed with these pineapple upside down cookies.

What are Pineapple Upside Down Cookies?

So, what exactly are these magical little treats I’m raving about? Think of them as bite-sized versions of that beloved pineapple upside down cake, but in cookie form! Instead of a big cake pan, we’re concentrating all that caramelized goodness into individual cookie tops. Essentially, you get a soft, tender cookie base, crowned with a sweet, slightly tangy pineapple topping that’s been kissed by the heat until it’s wonderfully gooey and caramelized. It’s the perfect balance of moist cake-like cookie and that irresistible fruity, buttery topping. It’s like a little vacation for your taste buds! The name itself, “pineapple upside down cookies,” comes from the baking method – we bake them upside down, so the fruit topping caramelizes right on top, creating that signature look and incredible flavor. It’s such a clever way to get so much flavor packed into such a small, irresistible package.

How do I make Pineapple Upside Down Cookies?

Quick Overview

The beauty of these pineapple upside down cookies lies in their straightforward assembly. We’ll create a simple, delicious caramel base in our muffin tin, top it with juicy pineapple rings (or pieces!), and then nestle our tender Cookie Dough right on top. They bake up in a flash, creating those iconic caramelized tops. It’s a truly magical transformation you can witness right in your oven!

Ingredients

For the Main Batter:

Here’s what you’ll need for the cookie dough itself. I always opt for unsalted butter because it gives me more control over the saltiness of the final cookie, but if you only have salted, just reduce the added salt by a quarter teaspoon. And please, use fresh eggs! They really make a difference in the texture and rise. I’ve tested this with a good quality all-purpose flour, and it works beautifully every time.

• 1 cup (2 sticks) unsalted butter, softened
• 1 1/2 cups granulated sugar
• 2 large eggs, room temperature
• 1 teaspoon vanilla extract
• 2 1/2 cups all-purpose flour
• 1 teaspoon baking powder
• 1/2 teaspoon salt

For the Filling:

This is where the magic happens! You can absolutely use fresh pineapple, but I find canned pineapple rings are just so convenient and work perfectly here. Just make sure to drain them well. If you prefer, you can chop the rings into smaller pieces. For a richer flavor, I sometimes add a touch of brown sugar to the caramel mixture, but granulated sugar works wonderfully too.

• 1/2 cup (1 stick) unsalted butter
• 3/4 cup packed light brown sugar
• 1 can (20 ounces) pineapple rings, drained well (reserve a little juice if you like for the glaze!)
• Maraschino cherries, halved (optional, but they add such a pretty pop of color!)

For the Glaze:

This glaze is optional, but I think it takes these cookies to the next level. It adds an extra layer of sweetness and shine. You can make it thicker or thinner depending on your preference – just adjust the liquid amount. I’ve even used some of the reserved pineapple juice for a subtle flavor boost!

• 1 cup powdered sugar
• 2-3 tablespoons milk or reserved pineapple juice

Step-by-Step Instructions

Step 1: Preheat & Prep Pan

First things first, get that oven preheated to 350°F (175°C). This is super important for even baking. Now, grab a standard 12-cup muffin tin. We’re going to make the caramelized topping right in here. Melt the 1/2 cup of butter for the filling and brush it generously into the bottom of each muffin cup. Don’t be shy with the butter – it’s what makes that delicious caramel layer! Then, sprinkle about a tablespoon of brown sugar evenly into each buttered cup. This is the foundation of our glorious pineapple topping.

Step 2: Mix Dry Ingredients

In a medium bowl, whisk together your flour, baking powder, and salt. Just give them a good stir to combine everything. This ensures the leavening agent and salt are evenly distributed, which means your cookies will have a consistent texture and rise. I always like to sift my flour for cookies, but for this recipe, just a good whisk works perfectly fine. We want to avoid overmixing later, so having these dry ingredients ready to go is key.

Step 3: Mix Wet Ingredients

In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This usually takes a few minutes with an electric mixer. Then, beat in the eggs one at a time, making sure each is fully incorporated before adding the next. Finally, stir in the Vanilla Extract. You should have a smooth, creamy mixture that smells absolutely divine.

Step 4: Combine

Now, it’s time to bring the wet and dry ingredients together. Gradually add the dry ingredients to the wet ingredients, mixing on low speed (or by hand) until just combined. Stop mixing as soon as you no longer see streaks of flour. Overmixing can lead to tough cookies, and we definitely don’t want that! The dough should be thick and lovely.

Step 5: Prepare Filling

This is where we prep our gorgeous pineapple topping. Take your drained pineapple rings and cut them in half or quarters, depending on the size of your muffin cups. You want them to fit nicely in the bottom of each cup. If you’re using maraschino cherries, have those halved and ready to go too. They’re purely for looks, but oh, what a lovely look they give!

Step 6: Layer & Swirl

Now for the fun part! Place a piece of pineapple in the bottom of each prepared muffin cup, on top of the brown sugar mixture. If you’re using cherries, nestle a half cherry into the center of each pineapple piece. Then, dollop about 1 to 2 tablespoons of cookie dough over the pineapple in each cup, spreading it gently to cover the fruit. You don’t need to be perfectly neat; a little rustic charm is part of their appeal!

Step 7: Bake

Pop that muffin tin into your preheated oven and bake for about 20-25 minutes. You’re looking for the cookies to be golden brown around the edges and a toothpick inserted into the cookie dough (not the pineapple!) to come out clean. Keep an eye on them, as oven temperatures can vary. I always start checking around the 20-minute mark.

Step 8: Cool & Glaze

Once they’re baked, let the cookies cool in the muffin tin for about 10 minutes. This is crucial for them to set up and for the caramel to unmelt. Then, carefully invert the muffin tin onto a wire rack to release the cookies. If any stick, gently coax them out with a knife. While they’re cooling a bit more, whisk together the powdered sugar and milk or pineapple juice for the glaze until smooth. Drizzle this over the warm cookies. The glaze will set up as they cool completely.

Step 9: Slice & Serve

Once they’ve cooled and the glaze has set, your beautiful pineapple upside down cookies are ready to be enjoyed! You can serve them warm or at room temperature. The smell alone as they’re cooling is enough to make your stomach rumble. They’re just perfect!

What to Serve It With

These pineapple upside down cookies are so wonderfully versatile, they truly fit into any occasion. For a cozy breakfast, I love serving them alongside a hot cup of coffee or a strong black tea. The sweetness of the cookie is the perfect counterpoint to a bitter brew. They also make a fantastic addition to a brunch spread. Imagine them arranged on a pretty platter next to some fresh fruit salad, a frittata, and maybe some crispy bacon. They add a touch of elegance and a delightful burst of flavor. As a dessert, they’re a dream! Serve them warm with a scoop of vanilla bean Ice Cream or a dollop of whipped cream. The contrast of the warm, gooey cookie with cold ice cream is just heavenly. My family also loves them as a special after-school snack. They’re so much more satisfying than a granola bar! I’ve even packed them for picnics and road trips; they hold up wonderfully. My kids always beg for them when we’re heading out somewhere, and honestly, I’m always happy to oblige!

Top Tips for Perfecting Your Pineapple Upside Down Cookies

Over the years, I’ve learned a few little tricks that really make these pineapple upside down cookies shine. First, about the pineapple: make absolutely sure it’s well-drained. Excess moisture can make your caramel watery, and we want that rich, thick consistency. If your pineapple rings seem very juicy, gently pat them dry with a paper towel before placing them in the muffin tin. For the brown sugar in the topping, make sure it’s nice and packed. This helps it melt down beautifully and create that lovely caramel. When it comes to the cookie dough, I can’t stress enough about not overmixing. Once you add the dry ingredients to the wet, mix just until they’re combined. A few small lumps are totally fine; in fact, they’re better than a tough cookie! If you find your dough is a little too sticky to handle, don’t worry. Just pop it in the fridge for about 15-20 minutes, and it will firm up nicely, making it much easier to scoop and spread over the pineapple. For the glaze, consistency is key. If it’s too thick, it’ll be hard to drizzle; if it’s too thin, it’ll just run off. Start with the lower amount of liquid and add more a teaspoon at a time until you reach your desired drizzling consistency. I’ve also found that using reserved pineapple juice for the glaze adds a subtle, delicious tropical note that complements the cookie perfectly. And one last tip: be patient with the cooling and inverting process. Letting them sit in the tin for that 10 minutes is crucial. Trying to pop them out too soon is how you end up with a messy pineapple-and-cookie jumble!

Storing and Reheating Tips

These pineapple upside down cookies are best enjoyed fresh, but they do store quite well, which is a big win! If you have any leftovers (which is rare in my house!), you can store them at room temperature in an airtight container for up to 3 days. Make sure they’re completely cooled before sealing the container, or you might end up with condensation, which can make them a bit soggy. If you plan on keeping them longer, or if your kitchen is particularly warm, refrigerating them is a great option. Store them in an airtight container in the fridge for up to a week. They’ll still be delicious, though I personally prefer them at room temperature or slightly warmed. When you’re ready to reheat, you can pop a few in a toaster oven or a conventional oven at a low temperature (around 300°F or 150°C) for just a few minutes until they’re warmed through and the caramel is soft again. Be careful not to overheat them, or they can dry out. Freezing is also an option if you’ve made a huge batch and want to save them for later. Wrap each cooled cookie individually and tightly in plastic wrap, then place them in a freezer-safe bag or container. They should keep well in the freezer for up to 2-3 months. To thaw, simply remove them from the freezer and let them come to room temperature, or reheat gently as described above. For the glaze, I usually add it *after* baking and cooling. If you’re planning to freeze them, I’d recommend glazing them *after* they’ve been thawed and gently reheated, or just dusting them with a little powdered sugar for a simpler finish.

Frequently Asked Questions

Final Thoughts

Seriously, if you’re looking for a recipe that brings instant smiles and a whole lot of comforting flavor, these pineapple upside down cookies are it. They capture that nostalgic taste of a classic dessert but in a wonderfully convenient cookie format. They’re perfect for when you want something a little sweet, a little tropical, and a whole lot of delicious without committing to a full cake. I hope you give these a try and that they bring as much joy to your kitchen as they do to mine. If you love this recipe, you might also enjoy my chewy coconut macaroons or my classic Chocolate Chip Cookies – they’re all family favorites! Let me know in the comments below how yours turn out, and if you have any fun variations you’ve tried. I can’t wait to hear all about it! Happy baking, everyone!

Pineapple Upside Down Cookies

These Pineapple Upside Down Cookies are a delightful twist on the classic cake, featuring a chewy cookie base topped with caramelized pineapple and a maraschino cherry.

Prep : 10 Total : 25 minutes

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Ingredients

  

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Cookie Dough

• 1 cup unsalted butter softened
• 1.5 cup granulated sugar
• 2 large eggs
• 1 teaspoon vanilla extract
• 2.5 cup all-purpose flour
• 1 teaspoon baking soda
• 0.5 teaspoon salt

Pineapple Topping

• 1 can crushed pineapple drained well
• 0.5 cup packed brown sugar
• 0.25 cup unsalted butter melted
• 24 maraschino cherries stems removed

Instructions

 

Preparation Steps

• Preheat oven to 375°F (190°C). Line baking sheets with parchment paper.
• In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  1 cup unsalted butter
• Beat in the eggs one at a time, then stir in the vanilla extract.
  1 cup unsalted butter
• In a separate medium bowl, whisk together the flour, baking soda, and salt.
  1 cup unsalted butter
• Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Do not overmix.
• In a small bowl, combine the drained crushed pineapple, brown sugar, and melted butter. Stir until well mixed.
  1 cup unsalted butter
• Drop rounded tablespoons of cookie dough onto the prepared baking sheets.
• Place a spoonful of the pineapple mixture on top of each cookie dough ball.
• Gently press a maraschino cherry into the center of the pineapple mixture on each cookie.
  1 cup unsalted butter
• Bake for 10-13 minutes, or until the edges are golden brown and the center is set.
• Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.

Notes

Store cooled cookies in an airtight container at room temperature for up to 3 days.