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This hearty pineapple upside-down sugar cookie recipe transforms the classic cake into a convenient, handheld treat that captures all the caramelized sweetness without the fuss. The combination of buttery cookie base with caramelized pineapple topping creates an irresistible twist on two beloved desserts.
I created these cookies during a summer family reunion when I wanted something special but didn't have time for a full cake. My grandmother, who was famous for her upside-down cake, declared these cookies even better than her original recipe.
Ingredients
- Unsalted butter at room temperature: crucial for proper creaming and tender texture
- Granulated sugar: provides the perfect sweetness and helps create those crisp edges
- Large egg: acts as a binder for the cookie dough
- Vanilla extract: enhances all the flavors without overpowering
- All purpose flour: gives structure while keeping cookies tender
- Baking soda: provides just enough lift for the perfect cookie texture
- Salt: balances the sweetness and enhances flavor
- Canned pineapple rings: bring the classic upside down cake flavor in a convenient form
- Extra granulated sugar for sprinkling: creates that signature caramelized top
Step-by-Step Instructions
- Prepare Your Oven and Pans:
- Preheat your oven to 350°F and line baking sheets with parchment paper which prevents sticking and makes cleanup effortless. The parchment also helps the cookies bake more evenly by providing insulation from direct heat.
- Create The Cookie Base:
- Cream the softened butter and sugar for a full 3 4 minutes until truly light and fluffy. This step incorporates air into the mixture which is essential for creating the perfect cookie texture. The mixture should lighten in color noticeably from yellow to almost white.
- Add Wet Ingredients:
- Beat in the egg and vanilla until completely incorporated. The mixture should look smooth and glossy. Make sure to scrape down the sides of the bowl to ensure everything mixes evenly.
- Incorporate Dry Ingredients:
- Whisk the flour, baking soda, and salt together to distribute the leavening evenly. Add this mixture gradually to your wet ingredients, mixing just until a cohesive dough forms. Overmixing at this stage will develop too much gluten, resulting in tough cookies.
- Shape The Cookies:
- Roll the dough into consistent balls about 1 1/2 tablespoons each. This size creates the perfect base for a pineapple ring. Gently flatten each ball into a disk, leaving at least 2 inches between cookies for proper spreading.
- Add The Pineapple Topping:
- Place a well dried pineapple ring on each cookie, pressing gently to adhere. The pineapple must be thoroughly patted dry to prevent excess moisture from making the cookies soggy during baking.
- Finish And Bake:
- Sprinkle additional sugar over each pineapple ring to create that gorgeous caramelized finish. Bake for 12 14 minutes, watching for golden edges that signal perfect doneness. The centers may look slightly underdone but will set as they cool.
- Cooling Process:
- Allow cookies to rest on the hot baking sheet for 5 minutes to set up properly. Then transfer to a wire rack where air can circulate around the entire cookie, preventing sogginess from trapped steam.
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Pineapple is actually the secret star of this recipe. I discovered through multiple tests that thoroughly drying the pineapple rings is absolutely crucial. One batch I made with hastily dried pineapple became sadly soggy, while properly dried rings created that perfect caramelized topping that makes these cookies so special.
Storage Solutions
These pineapple upside down cookies require specific storage considerations due to their fruit topping. Store them in a single layer in an airtight container at room temperature for up to 4 days. Avoid stacking them as the moist pineapple topping can make cookies stick together or soften the bottom of cookies placed above them. If you need to stack them for storage, place parchment paper between layers to prevent sticking.
Easy Variations
While the classic pineapple version is delightful, this versatile cookie base works beautifully with other fruit toppings too. Try thinly sliced peaches or apricot halves for a summery variation. For an autumnal twist, thinly sliced apples sprinkled with cinnamon sugar create a caramel apple cookie experience. You can even use maraschino cherries alone for a simpler but equally festive cookie that children especially love.
Serving Suggestions
These cookies transform into an elevated dessert when served slightly warm with a scoop of vanilla ice cream on the side. For brunch gatherings, pair them with coffee flavored with a splash of coconut cream to complement the tropical pineapple notes. They also make a wonderful addition to holiday cookie exchanges since they stand out among the typical chocolate and sugar cookie offerings with their bright flavor and distinctive appearance.
The History Behind The Recipe
Pineapple upside down cake became popular in America during the 1920s after the invention of canned pineapple and the promotion of Hawaiian pineapple by companies like Dole. This cookie version maintains the nostalgic appeal while adapting to modern preferences for individual portions and portable treats. The combination creates a wonderful conversation starter at gatherings as guests recognize the familiar flavors in this innovative presentation.
Common Queries
- → How do you prevent soggy cookies from the pineapple topping?
Thoroughly drain and pat the pineapple rings dry before placing them on your dough. Excess moisture can lead to soggy cookies, so this step is essential for crisp edges.
- → Can I use fresh pineapple instead of canned?
Yes, fresh pineapple can be used as long as it’s sliced into rings and properly dried to avoid excess moisture. Canned rings are more uniform and convenient, but both work well.
- → Can these cookies be stored, and for how long?
Store in an airtight container at room temperature for up to four days. For the best texture, enjoy them within the first two days.
- → What’s the best way to achieve caramelized, golden tops?
Sprinkle extra granulated sugar over each pineapple ring before baking. An additional 1-2 minutes in the oven can help deepen the golden color.
- → Can I add maraschino cherries for a classic touch?
Absolutely! Place a maraschino cherry in the center of each pineapple ring before baking for nostalgic flavor and a vibrant pop of color.