Pineapple Upside Down Sugar Cookies Recipe

So you’re craving something tropical, sweet, and totally Instagram-worthy—but don’t feel like making a full-on cake? Same. That’s where these Pineapple Upside Down Sugar Cookies come in. They’ve got all the caramelized pineapple vibes of a classic upside-down cake but in the perfect bite-sized cookie form. Basically, it’s a mini vacation for your taste buds.

Why This Recipe is Awesome

Let’s be real—this recipe is ridiculously easy. Even if your baking skills are “I can burn water,” you’ll still end up with something edible (and adorable). The cookies are soft, chewy, and packed with pineapple-y caramel goodness, making every bite a sweet little hug. Bonus: they make your kitchen smell like a tropical paradise without requiring a plane ticket.

Other highlights:

• Perfectly portable—great for snacks, parties, or bribes.
• Customizable—swap pineapples for peaches, cherries, or whatever fruit makes your soul happy.
• Impressively fancy-looking without spending hours decorating.

Ingredients You’ll Need

Here’s what you need to make magic happen:

• 1 cup unsalted butter (softened, not melted)
• 1 cup granulated sugar
• 1 large egg
• 1 tsp vanilla extract
• 2 1/2 cups all-purpose flour
• 1/2 tsp baking powder
• 1/4 tsp salt
• 1/2 cup brown sugar (for that caramelized effect)
• 1/4 cup crushed pineapple (drain it well, we’re not making a soggy mess)
• Optional: maraschino cherries or candied pineapple for decoration

Pro tip: don’t skip the draining on the pineapple—soggy cookies are a sad cookie.

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Step-by-Step Instructions

1. Preheat & prep: Heat oven to 350°F (175°C). Line a baking sheet with parchment paper.
2. Mix the base: Cream together butter and sugar until fluffy. Beat in the egg and vanilla.
3. Dry ingredients: In a separate bowl, whisk flour, baking powder, and salt. Gradually mix into wet ingredients.
4. Shape the cookies: Roll dough into 1–inch balls. Flatten slightly with your palm.
5. Caramelize: Sprinkle a little brown sugar on top of each cookie. Top with a small piece of pineapple (and cherry if desired).
6. Bake: 12–15 minutes until edges are lightly golden.
7. Cool & enjoy: Let them cool for 5 minutes on the sheet, then transfer to a wire rack. Try not to eat them all immediately.

Common Mistakes to Avoid

• Skipping preheating the oven—don’t do it, rookie mistake.
• Using too wet pineapple—you’ll end up with cookies that look like a soggy science experiment.
• Overbaking—soft cookies are the goal; crunchy ones are sad cookies.
• Ignoring the brown sugar topping—this is what makes it “upside-down” magic happen.

Alternatives & Substitutions

• Butter: Margarine works but IMO, it’s just not as dreamy.
• Pineapple: Peaches, mango, or even berries work if you want to mix it up.
• Brown sugar topping: Maple sugar or coconut sugar can give a fun twist.
• Gluten-free: Swap in a 1:1 gluten-free flour blend; texture may vary slightly.

FAQs

Can I make these ahead of time?

Absolutely! They keep in an airtight container for 3–4 days. Not that they’ll last that long…

Can I freeze the dough?

Yes! Shape into balls and freeze on a tray, then toss straight into the oven (add a minute or two to bake).

Do I really need to drain the pineapple?

Yes. Yes. Seriously. Soggy cookies = sadness.

Can I use canned pineapple chunks instead of crushed?

Totally, just chop them finely so each cookie gets a bit of pineapple goodness.

Are these cookies soft or crunchy?

Soft and chewy, just like a sweet little tropical hug.

Can I double the recipe?

Go wild! Baking sheet space permitting, you can double or triple this recipe.

Final Thoughts

So there you have it: easy, fun, and oh-so-delicious Pineapple Upside Down Sugar Cookies. They’re perfect for parties, snacks, or just a treat for yourself (because why not?). Now go impress someone—or yourself—with your new tropical cookie skills. You’ve earned it!