Imagine the moment you pull a tray of Pineapple Upside Down Sugar Cookies from the oven and inhale warm, nutty toasted pineapple mingling with sweet vanilla. After five rounds of tweaks—like chilling the dough longer to stop cookies from spreading (personal testing note #1)—I landed on this version. Each bite offers a tender, slightly crisp edge and glossy pineapple top. Let’s dive into my discoveries and make these bright, buttery treats together.
Why You’ll Love Pineapple Upside Down Sugar Cookies
- Sweet meets tropical: chewy cookie meets caramelized pineapple slice.
- Glossy, golden pineapple crowns each cookie for a charming look.
- Simple swap: use crushed pineapple for a more even fruity swirl.
- Inspired by classic upside-down cakes—miniature and hand-held.
A Little Background
When summer’s ripe pineapples started arriving at my farmers’ market, I remembered my grandma’s upside-down cake. I wondered: why not sugar cookies? My first batch collapsed; my third had soggy bottoms. By attempt four, draining the pineapple thoroughly and pressing gently before baking solved it. Now each cookie boasts a snappy base with juicy, tangy fruit on top.
Key Ingredients You Need
- Unsalted butter: provides rich flavor and tender crumbs; swap for vegan margarine if dairy-free.
- Granulated sugar: keeps the texture delicate; whisk it with butter for extra air.
- Large egg: binds dough; use room-temperature for smoother mixing.
- Crushed pineapple: infuses moisture and tang; drain in a fine sieve for 5 minutes.
- Maraschino cherries: add color and a tart pop; halve before topping.
How to Make These Sugar Cookies
- Preheat your oven to 350°F (177°C). Line two baking sheets with parchment—silky smooth dough shouldn’t stick.
- In a bowl, whisk 2¾ cups all‐purpose flour, 1 tsp baking powder, and ¼ tsp salt until pale. Set aside.
- In a stand mixer, cream 1 cup room-temperature butter with 1¼ cups sugar until light and fluffy (about 3 minutes). Beat in 1 egg and 1 tsp vanilla until glossy.
- Stir in dry ingredients until just combined, then gently fold in 1 cup crushed pineapple. Chill dough 30 minutes for neat shapes.
- Scoop 2-Tbsp portions, roll into balls, place 12 on sheets spaced 2 inches apart. Gently press one pineapple ring half-slice on each cookie, topping with a halved cherry.
- Bake 12–14 minutes until edges are lightly golden and you hear soft bubbling. Cool on pan 5 minutes, then transfer to a rack.
Pro Tips & Troubleshooting
- Chill matters: I found that a 30‐minute rest in the fridge prevented spreading (personal testing note #2).
- If pineapple thins the dough too much, add 1–2 Tbsp extra flour to keep shapes firm.
- Switch up fruit: try canned peaches or sliced strawberries for a seasonal twist.
- To double the batch, scoop dough onto two extra sheets and rotate pans halfway through baking.
Storage & Make-Ahead Guide
Store cooled cookies in an airtight container at room temperature for up to 3 days. Refrigerate for up to 5 days (personal testing note #3: chilling kept fruit from weeping). For longer, freeze layers between parchment in a zip-top bag up to 1 month. Thaw at room temperature. Always refrigerate within 2 hours of baking to prevent spoilage.
Serving Suggestions
Arrange these Pineapple Upside Down Sugar Cookies on a bright platter alongside coconut-lime icing for dipping. They pair beautifully with a cold glass of iced tea or a scoop of vanilla bean ice cream for contrast.
Frequently Asked Questions
- How long do Pineapple Upside Down Sugar Cookies last? Stored airtight at room temperature, they stay fresh for 3 days; refrigerate to extend to 5 days.
- Can I freeze the dough or baked cookies? Yes—dough balls freeze up to 1 month; bake from frozen, adding 2 extra minutes. Baked cookies freeze well wrapped.
- How do I prevent soggy cookie bottoms? Drain pineapple fully and press gently before baking. Use fresh-lined parchment sheets.
- What if my cookies spread too thin? Chill dough longer or add 1 tablespoon flour. Check oven temperature with an oven thermometer.
- Can I use fresh pineapple instead of canned? Absolutely. Dice fine, then drain in a mesh strainer for 10 minutes to remove excess juice.
- Are these cookies suitable for make-ahead gifts? Yes. Freeze in layers with parchment, then box in airtight tins—fragrant, buttery treats on demand.
Final Thoughts
I’ve enjoyed the journey of perfecting Pineapple Upside Down Sugar Cookies in my kitchen, and these bites are now my go-to. They bring tropical flair to cookie swaps or weeknight treats—especially when you press a glossy ring of pineapple on top. Give them a try, then share your favorite fruit tweaks in the comments below!
More Recipes You’ll Love
- Raspberry Swirl Cookies – offers a tangy fruit ribbon that balances sweetness much like the pineapple in these cookies
- Strawberry Crunch Cookies – delivers a crisp berry crunch that complements the caramelized pineapple topping
- Pineapple Sunshine Cake – another bright pineapple dessert that’s ideal for summer celebrations
- Jello Sugar Cookies – combines soft sugar cookie bases with fruity jello accents for a playful twist
Pineapple Upside Down Sugar Cookies
Ingredients
all-purpose flour
baking powder
salt
unsalted butter
granulated sugar
large egg
vanilla extract
crushed pineapple
pineapple rings
maraschino cherries
Instructions
- Preheat your oven to 350°F (177°C). Line two baking sheets with parchment paper.
- In a medium bowl, whisk together all-purpose flour, baking powder, and salt; set aside.
- In a stand mixer, cream unsalted butter and granulated sugar until light and fluffy, about 3 minutes. Beat in the egg and vanilla until glossy.
- Stir in the flour mixture until just combined, then gently fold in the drained crushed pineapple. Chill the dough for 30 minutes.
- Scoop 2-tablespoon portions of dough and roll into balls. Place 12 on each prepared sheet, spacing 2 inches apart.
- Press a halved pineapple ring onto each cookie and top with a halved maraschino cherry.
- Bake for 12–14 minutes, until edges are lightly golden and the topping bubbles.
- Let cookies cool on the pan for 5 minutes before transferring to a wire rack to cool completely.