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These pineapple upside-down cookies are my go-to summer treat when I want all the flavors of the beloved cake but need something quick and easy to share at gatherings. With caramelized pineapple and a cherry-topped finish, each cookie is both delightful and nostalgia-filled. Their bright look and tender bite never fail to remind me of carefree family afternoons on the porch, cookies vanishing almost as fast as I can bake them.
I first tried these when I needed a dessert everyone could grab and go and they have quickly become the most-requested sweet at my summer table. My kids absolutely love flipping them over to see the gooey topping reveal.
Ingredients
- Unsalted butter: gives that rich melt-in-your-mouth texture look for butter that smells sweet and creamy
- Granulated sugar: brings both softness and the right sweetness use fine sugar to ensure smooth creaming
- Large egg: binds everything and creates a pillowy dough choose free-range eggs when possible
- Vanilla extract: adds warmth and layers of flavor real vanilla is best if you have it
- All-purpose flour: provides structure sift before measuring for the lightest cookies
- Baking powder: creates a tender yet sturdy bite check it is fresh for best lift
- Salt: brightens and balances every flavor a high-quality sea salt adds subtle complexity
- Brown sugar: becomes caramel with the topping lighter or dark according to your sweetness preference
- Melted butter: in the topping makes for that classic syrupy finish be sure it is fully melted
- Pineapple rings or tidbits: add sweetness and juiciness use canned or fresh just pat dry for best texture
- Maraschino cherries: give those pops of color and bright flavor buy good quality ones for best taste
Step-by-Step Instructions
- Prepare the Cookie Dough:
- Preheat your oven to 350 F and prepare your baking sheet with parchment or a silicone mat which keeps things easy to clean. Cream together the softened butter and sugar until fluffy and pale this creates soft cookies that hold their shape well. Add the egg and vanilla beating until you get a smooth glossy batter so no streaks remain. In a different bowl combine flour baking powder and salt with a good whisk to distribute everything evenly. Slowly mix the dry ingredients into the wet only until you see no more flour patches for the softest cookies.
- Prepare the Topping:
- Stir melted butter and brown sugar together until it looks like a thick caramel paste this is what turns sticky golden under each cookie. Spoon about a teaspoon of this mixture for each cookie space out on your lined sheet.
- Assemble the Cookies:
- Place a little piece of pineapple on each mound of brown sugar topping and then nestle half a cherry in the center to echo the classic look. Take a scoop of dough flatten gently by hand and cover the pineapple and cherry sealing the edges so the caramel stays put.
- Bake the Cookies:
- Slide the tray into your oven and bake for between twelve and fifteen minutes or until you see the edges golden and the cookies set. Let them cool for roughly five minutes before moving to a rack to avoid breaking while hot.
- Serve and Enjoy:
- Once fully cool flip each cookie so the topping decorates the top this way you reveal the sunny pineapple and shiny cherry just like the classic cake.
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One of my favorite bits is sneaking warm pineapple pieces from the tray but the best part is seeing everyone’s faces when they flip the cookies and find a jewel-bright cherry beaming on top My grandmother always added a pinch of salt to the topping and I find it makes the caramel even more delicious
Storage Tips
Keep cookies in an airtight container at room temperature for two to three days If you want to store them longer layer parchment between cookies and freeze for up to two months Thaw at room temp before serving The topping stays glossy and caramelized even after freezing
Ingredient Substitutions
No maraschino cherries Try sweet dried cranberries or real fresh cherries Allergic to eggs Swap in a flax egg and bake as usual If you want gluten free simply choose a one-for-one baking blend Measure flour carefully for best results
Serving Suggestions
Serve these with iced tea or cool lemonade for a perfect summer snack For presentation set cookies on a platter with extra pineapple pieces or serve warm with a scoop of vanilla ice cream They are especially adorable for kids’ parties or retro-themed gatherings
A Little History
Pineapple upside-down cake first became popular after canned pineapple was introduced to US home bakers in the early twentieth century These cookies are a perfect modern nod to that good old-fashioned hospitality in a fun bite-sized way
Recipe FAQs
- → How do I prevent the cookies from sticking to the baking sheet?
Line your baking sheet with parchment paper or a silicone baking mat. This helps the caramelized topping release easily and makes cleanup simple.
- → Can I use fresh pineapple instead of canned?
Absolutely! Use fresh pineapple cut into small tidbits. Just pat them dry with a paper towel to keep excess moisture from affecting the cookies.
- → What can I substitute for maraschino cherries?
Fresh cherries or dried cranberries work well as alternatives. They add both color and a sweet-tart flavor option.
- → How should I store these cookies?
Keep cookies in an airtight container at room temperature for up to 3 days. Separate layers with parchment to keep the toppings neat.
- → How do I make the cookies hold their shape better?
If your dough is very soft, chill it in the fridge for 10-15 minutes before shaping. Also, use butter that is slightly cool to the touch.