Tropical Pineapple Butter Cookies

This perfectly sweet pineapple upside-down sugar cookie recipe transforms the classic cake into handheld treats that bring tropical flavor to your cookie jar. The juicy pineapple rings caramelize beautifully on top of buttery sugar cookies, creating an irresistible combination that's easier than making a traditional upside-down cake.

I first made these cookies for a summer potluck when I needed something quick but memorable. The way the pineapple caramelizes slightly during baking reminds me of the upside-down cakes my grandmother used to make, but in a much more portable and shareable form.

Ingredients

• Unsalted Butter: softened at room temperature allows for proper creaming with sugar creating that perfect cookie texture
• Granulated Sugar: provides sweetness and helps create those slightly crisp edges
• Large Egg: binds everything together and adds moisture to the dough
• Vanilla Extract: enhances the buttery flavor and complements the tropical pineapple beautifully
• All Purpose Flour: provides structure to the cookies use unbleached for best flavor
• Baking Soda: helps the cookies rise and spread slightly during baking
• Salt: balances the sweetness and enhances all other flavors
• Canned Pineapple Rings: are convenient and consistent make sure to drain and pat them very dry
• Additional Sugar: for sprinkling creates a delicate caramelized finish on the pineapple

Step-by-Step Instructions

Prepare Your Oven And Trays:

Preheat your oven to 350°F and line baking trays with parchment paper. The parchment prevents sticking and makes cleanup easier especially important with the sugary pineapple topping.

Create The Cookie Base:

Cream together softened butter and sugar until the mixture becomes noticeably lighter in both color and texture about 2 3 minutes with an electric mixer. This incorporates air into the dough for proper texture.

Add Wet Ingredients:

Beat in the egg and vanilla extract until the mixture appears smooth and well combined. The egg should be fully incorporated with no streaks visible.

Incorporate Dry Ingredients:

Whisk together flour baking soda and salt in a separate bowl then gradually add to the wet ingredients. Mix just until a soft dough forms overmixing will develop gluten and make cookies tough.

Form The Cookies:

Scoop approximately 2 tablespoons of dough per cookie onto prepared trays spacing them 2 inches apart. The cookies will spread during baking so adequate spacing prevents them from merging together.

Add Pineapple Topping:

Gently press a dried pineapple ring onto each mound of cookie dough flattening slightly. Be sure the pineapple rings are very well drained and patted dry to prevent excess moisture from making cookies soggy.

Sprinkle With Sugar:

Dust a small amount of granulated sugar over the pineapple tops. This creates a beautiful sparkle and helps the pineapple caramelize during baking.

Bake To Perfection:

Bake for 11 13 minutes until cookies appear lightly golden around the edges while still soft in the center. They will continue cooking slightly on the hot tray after removal.

Cool Properly:

Allow cookies to cool on the baking tray for a few minutes before transferring to a wire rack. This short rest period allows them to set up enough to move without breaking.

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The pineapple is truly the star ingredient here. I once tried making these with fresh pineapple slices that I had caramelized beforehand and while delicious it was much more work with similar results. The convenience of canned pineapple rings makes this recipe accessible for busy bakers while still delivering that tropical flavor punch that everyone loves.

Recipe FAQs

→ How do I ensure my pineapple doesn't make the cookies soggy?

Thoroughly drain the canned pineapple rings and pat them dry with paper towels before placing them on the cookie dough. This removes excess moisture that could make your cookies soggy. For extra insurance against sogginess, you can also place the drained pineapple rings on paper towels for 10-15 minutes before using them.

→ Can I use fresh pineapple instead of canned?

Fresh pineapple can be used, but it contains more moisture than canned. If using fresh, cut thin slices (about 1/4 inch thick), place them on paper towels, and press gently to remove excess juice. You may also want to briefly sauté fresh pineapple pieces in a bit of butter and sugar to pre-caramelize them before adding to the cookies.

→ How do I store these cookies to maintain freshness?

Store the cookies in a single layer in an airtight container at room temperature for up to 3 days. Place parchment paper between layers if you need to stack them. For longer storage, freeze the cookies in a single layer for up to 2 months in a freezer-safe container.

→ Can I add other ingredients to enhance the tropical flavor?

Absolutely! Consider adding 1/2 cup shredded coconut to the cookie dough, a tablespoon of rum extract instead of vanilla, or a sprinkle of brown sugar instead of granulated sugar on top for more caramelization. You could also add 1/4 teaspoon of ground ginger or a tablespoon of finely chopped maraschino cherries in the center of each pineapple ring.

→ Why did my cookies spread too much during baking?

Over-spreading typically happens when the butter is too warm or the dough wasn't chilled. For better results, make sure your butter is softened but not melty. If your dough feels very soft after mixing, refrigerate it for 20-30 minutes before scooping and baking. Also, make sure your baking sheets are cool before placing new batches of dough on them.

→ Can these cookies be made ahead for a party?

Yes! You can prepare the cookie dough up to 2 days in advance and store it covered in the refrigerator. Alternatively, you can bake the cookies a day before your event and store them in an airtight container. For the freshest taste, bake them the same day you plan to serve them, as the pineapple topping is best enjoyed within 24 hours.