Oh, the smell of pineapple upside-down cake! It just takes me right back to childhood. That sweet, caramelized pineapple and cherry topping, the tender cake… it’s pure comfort, right? Well, guess what? I’ve figured out how to capture all that amazing flavor in a perfectly chewy cookie! These Pineapple Upside-Down Cookies are seriously addictive. My grandma used to make the cake all the time, and whenever pineapple season rolled around, I’d beg her for it. Now, I can have that taste anytime I want, right in the palm of my hand. It’s my little way of keeping those happy memories alive in the kitchen!
Why You’ll Love These Pineapple Upside-Down Cookies
Seriously, these cookies are a little slice of heaven! Here’s why you’re gonna be obsessed:
- That Nostalgic Flavor: They taste *exactly* like classic pineapple upside-down cake, but in chewy cookie form!
- Perfectly Chewy Texture: We’re talking soft, chewy goodness with those little bursts of pineapple.
- Super Easy to Make: Even if you’re not a pro baker, these come together in a flash. Trust me!
- Quick Treat: You can whip these up in no time for unexpected guests or just a Tuesday afternoon craving.
Gather Your Ingredients for Pineapple Upside-Down Cookies
Alright, let’s get our cookie-making pantry stocked! When I first tried to recreate that pineapple upside-down cake magic in a cookie, I realized the ingredients are super important for nailing that flavor. So, here’s what you’ll need to grab:
First up, we’ve got 1 cup (that’s two sticks!) of unsalted butter, softened. Getting the butter just right – softened, not melted – is key for getting that fluffy, creamy base. Next, 1 1/2 cups of granulated sugar. This helps with that wonderful chewiness and sweetness we’re aiming for.
For richness, we’re using 2 large eggs, and a teaspoon of vanilla extract always makes things taste more like home, right? Then, for our dry team: 3 cups of all-purpose flour, 1 teaspoon of baking soda to help them spread just so, and 1/2 teaspoon of salt to balance everything out. Oh, and don’t forget some kosher salt if you’re finishing them with a little sprinkle – check out this guide for kosher salt; it’s fantastic for bringing out flavors!
Now for the stars of the show! You’ll need 1/2 cup of crushed pineapple, but make sure it’s really well-drained. This prevents any soggy cookie situations, trust me. And those pretty little cherries? Grab 1/4 cup of maraschino cherry halves, also drained. They’re like the little jewels on top! Finally, a bit of 1/4 cup of brown sugar to sprinkle over the top before baking adds that extra caramel touch that just finishes them off perfectly.
Step-by-Step Guide to Making Pineapple Upside-Down Cookies
Alright, let’s get these cookies into the oven! Watching them bake is the best part, but getting the dough just right is where the magic starts.
Preparing the Cookie Dough for Pineapple Upside-Down Cookies
First things first, make sure your oven is preheated to 350°F (175°C). I like to line my baking sheets with parchment paper because it makes cleanup a breeze and helps the cookies bake evenly, preventing them from sticking. In a nice big bowl, we’re going to cream together that softened butter and the granulated sugar. You want to beat them until they’re nice and fluffy – it usually takes a couple of minutes. Then, we add the eggs one at a time, mixing well after each one, and stir in that lovely vanilla extract. In a separate bowl, whisk your flour, baking soda, and salt together. Now, gradually add the dry stuff to the wet ingredients, mixing until it’s just combined. Seriously, don’t overmix here; a few little streaks of flour are okay! For balancing flavors, using good salt is a must, it really makes a difference. Check out this guide for kosher salt; it’s fantastic for bringing out flavors!
Assembling and Baking Your Pineapple Upside-Down Cookies
Okay, time for the best part – the pineapple! Gently fold in that well-drained crushed pineapple. You don’t want to mash it up, just get it nicely distributed. Then, drop rounded tablespoons of this delicious dough onto your prepared baking sheets, leaving a bit of space between them since they’ll spread a tiny bit. Now for the super cute part: gently press a drained maraschino cherry half right into the center of each cookie. It just makes them look so professional! Finally, sprinkle the tops with that brown sugar. Pop them into the oven for about 10-12 minutes. You’re looking for the edges to be just lightly golden brown. Once they’re out, let them cool on the baking sheets for a few minutes before carefully moving them to a wire rack to cool completely. Patience is a virtue here, but oh, so worth it!
Tips for Perfect Pineapple Upside-Down Cookies
Okay, so you’ve got the recipe, but sometimes those little tricks make all the difference, you know? It’s like the cookies just *know* when you’ve paid attention to the details! My biggest tip? Really, truly drain that pineapple. I mean, press out as much liquid as you possibly can. Soggy pineapple means a sad, greasy cookie, and nobody wants that. You can even give it a gentle pat with a paper towel after draining if you’re feeling extra cautious.
Another thing I learned early on is about the dough consistency. If it feels a little too sticky, don’t be tempted to add tons more flour! Sometimes just chilling the dough for 15-20 minutes can work wonders. It makes it easier to scoop and keeps those cookies from spreading too much. And when they’re baking? Keep an eye on them! Ovens can be so different. You want that lovely golden edge, but don’t let them get too dark or they’ll be crunchy instead of chewy. Cooling them on the sheet for a few minutes before moving them to the wire rack is crucial, too. It lets them set up so they don’t fall apart.
Ingredient Notes and Substitutions for Pineapple Upside-Down Cookies
Little tweaks here can make a big difference! For the Pineapple Upside-Down Cookies, using crushed pineapple is really important. Make sure it’s the kind you find in the can, and *really* drain it well. If you get a little too much moisture, your cookies might spread out too much or become a bit too soft. You can even give it a gentle squeeze in a fine-mesh sieve.
As for those pretty red cherries? If you can’t find halves, chopped maraschino cherries work just fine! Or, if you’re feeling fancy and want to level up that pineapple flavor, you could totally add about a teaspoon of pineapple extract to the dough with the vanilla. Yum! I love playing around with flavors, and it reminds me of how versatile pineapple is, like in this amazing pineapple cucumber salad I make!
Storing and Reheating Your Delicious Pineapple Upside-Down Cookies
Alright, once these little gems are cooled, you’ll want to keep them tasting just as amazing as when they were fresh. The best way to store them is in an airtight container at room temperature. They’ll stay chewy and delicious for a good 3-4 days this way! If you somehow manage to have any left after that (lol, unlikely!), you can pop them in the fridge, but I find they’re best at room temp. No need to reheat usually, but if you want that just-baked warmth, a few seconds in the microwave or a quick zap in a toaster oven should do the trick!
Frequently Asked Questions About Pineapple Upside-Down Cookies
Can I use fresh pineapple in these cookies?
You know, while fresh pineapple is amazing in cakes, for these specific Pineapple Upside-Down Cookies, I really recommend sticking with canned crushed pineapple. Fresh pineapple has a lot more natural moisture and enzymes that can make the cookies too soft or even prevent them from setting properly. Plus, the canned stuff is already crushed, which makes things a lot easier! Just make sure you drain it super, super well.
Why are my Pineapple Upside-Down Cookies flat?
Oh, that happens sometimes! Usually, flat cookies are a sign of a few things. First, maybe the butter was too soft or even melted when you creamed it with the sugar – we want it softened, remember? Or, it could be that you overmixed the dough after adding the flour, which develops too much gluten. Also, ensure you’re not adding too much liquid, which is why draining that pineapple is *so* important! A good rule of thumb is to drop the dough, not spread it.
How long do these Pineapple Upside-Down Cookies stay fresh?
These cookies are surprisingly good at staying chewy and delicious for quite a few days! Once they’ve cooled completely, I like to store them in an airtight container at room temperature. They’re usually at their absolute best for about 3 to 4 days. They don’t really need refrigeration, but if it’s super hot where you are, popping them in the fridge might help them last a bit longer, though they can get a bit firmer.
Do I really need the cherry halves?
The cherry halves are totally a visual thing and add a little extra pop of flavor and color! They aren’t strictly essential for the cookie’s structure or taste, but they really do make these Pineapple Upside-Down Cookies look just like the upside-down cake we love. If you can’t find them or just don’t have them on hand, no worries! You can leave them off, or maybe try a tiny sliver of candied cherry if you happen to have some.
Estimated Nutritional Information
Okay, so let’s talk about what’s in these yummy Pineapple Upside-Down Cookies! Keep in mind that these numbers are just estimates, since everyone’s ingredients and brands can be a little different. But generally, one cookie has about 180 calories, 8 grams of fat (with saturated fat making up 5g of that), and 2 grams of protein. You’re also looking at around 25 grams of carbohydrates, with about 15 grams of that being sugar. Don’t forget the 1 gram of fiber and 70mg of sodium!
Share Your Pineapple Upside-Down Cookie Creations!
I absolutely LOVE seeing your baking adventures! If you make these yummy Pineapple Upside-Down Cookies, please share your photos with me! Leave a comment below to tell me how they turned out, or rate the recipe. You can also find me on social media and tag me – I’d be thrilled to see your creations! Want to connect or share your thoughts directly? Feel free to reach out via my contact page, or learn more about my baking journey on my about page!
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Pineapple Upside-Down Cookies
- Total Time: 32 min
- Yield: 24 cookies 1x
- Diet: Vegetarian
Description
These cookies capture the classic pineapple upside-down cake flavor in a chewy cookie form.
Ingredients
- 1 cup (2 sticks) unsalted butter, softened
- 1 1/2 cups granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 3 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1/2 cup crushed pineapple, well-drained
- 1/4 cup maraschino cherry halves, drained
- 1/4 cup brown sugar
Instructions
- Preheat your oven to 350°F (175°C). Line baking sheets with parchment paper.
- In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
- Beat in the eggs one at a time, then stir in the vanilla extract.
- In a separate bowl, whisk together the flour, baking soda, and salt.
- Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
- Gently fold in the drained crushed pineapple.
- Drop rounded tablespoons of dough onto the prepared baking sheets, about 2 inches apart.
- Press a maraschino cherry half into the center of each cookie.
- Sprinkle the tops of the cookies with brown sugar.
- Bake for 10-12 minutes, or until the edges are lightly golden brown.
- Let the cookies cool on the baking sheets for a few minutes before transferring them to a wire rack to cool completely.
Notes
- Ensure the crushed pineapple is very well-drained to prevent soggy cookies.
- You can substitute chopped maraschino cherries if halves are unavailable.
- For a stronger pineapple flavor, you can add 1 teaspoon of pineapple extract to the dough.
- Prep Time: 20 min
- Cook Time: 12 min
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 180
- Sugar: 15g
- Sodium: 70mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 25g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
Keywords: pineapple cookies, upside down cake cookies, fruit cookies, chewy cookies, dessert cookies