Pineapple Upside Down Sugar Cookies are the kind of treat you make when you want something familiar, but a little brighter and more fun. Maybe you love classic pineapple upside down cake, but you want it in a grab-and-go cookie form. Or your friends are coming over and you need a dessert that looks cute without a lot of fussy decorating. These cookies hit all the notes. They bake up soft and buttery, with glossy pineapple rings and a cherry peeking through like a little sunset. And yes, they smell like a tropical vacation coming out of your oven. 
How to Make Pineapple Upside-Down Cookies
This recipe keeps the heart of the original cake, just mini and hand-held. That means you get a layer of buttery brown sugar caramel under juicy pineapple and a bright cherry, all anchored by a soft sugar cookie. The key is setting up the muffin pan with the fruit and sugar first, then pressing in the dough, so everything bakes together and flips out in one pretty piece.
Step-by-Step
Prep your pan first. You’re going to use a standard muffin tin and lightly grease it so nothing sticks. In each cup, drop a small pat of butter and a teaspoon of brown sugar. When the cookies bake, that combo melts into a caramel that hugs the pineapple.
Next, nestle a pineapple piece in each cup. You can use a full ring trimmed to fit, half rings, or even small chunks if you prefer. Press a maraschino cherry into the center. If you love extra color, add two cherries in a cup and tuck them side by side.
For the cookie dough, start by beating room temperature butter and sugar until it looks fluffy and pale. That air makes the cookies tender. Mix in egg and vanilla. In a separate bowl, whisk flour, baking powder, and a pinch of salt. Combine the dry and wet just until they come together. Don’t overmix or the cookies can turn tough.
Scoop the dough and press a round into your palm. You want a disk that covers the fruit, about half an inch thick. Press it gently over the pineapple and cherry. The dough should sit snugly on top without squishing out the brown sugar too much.
Bake until the edges are lightly golden and the centers are set. Let the pan cool for a couple of minutes, then run a thin knife around each cup. Place a baking sheet on top of the muffin tin and flip with confidence. Lift the tin, and your cookies should slide out with glossy tops and caramel around the edges.
If you’re new to baking and want a little extra guidance on technique, this breakdown of cookie basics is a great primer: how to bake cookies like a pro.
“I made these for a picnic and people thought I bought them at a bakery. The flip reveal was the best part, and the cookies stayed soft for two days.”
Pro flip tip: If you’re nervous about sticking, cut parchment circles to fit the bottoms of the muffin cups before the butter and sugar. Peel off after flipping.
Equipment
You don’t need much: a standard muffin tin, two mixing bowls, a hand or stand mixer, and a rubber spatula. If you have a small cookie scoop, it makes portioning easier. A thin knife or offset spatula helps loosen the edges before flipping.
Shopping List
- Unsalted butter for the dough, plus a little for the pan
- Granulated sugar for the cookie dough
- Brown sugar for that classic caramel layer
- Egg for structure
- Vanilla extract for cozy flavor
- All-purpose flour, baking powder, and salt
- Maraschino cherries, drained and blotted dry
- Pineapple rings or tidbits, well drained
- Optional: a pinch of cinnamon or a splash of rum extract for extra warmth
About the fruit: Drain pineapple well. Extra liquid can lead to soggy tops and a hard time flipping. I like to pat the pineapple with paper towels before it goes into the muffin cups. Same with cherries. The drier they are, the shinier your cookies will look.
Yields: 12 to 14 cookies, depending on how generously you portion the dough. You can easily double the recipe for a party tray.
Storage & Freezing
Let the cookies cool completely before storing. The caramel sets as it cools and keeps the tops shiny. Slide them into an airtight container in a single layer if possible, or use parchment between layers. They’ll stay soft at room temperature for 2 to 3 days.
For longer storage, freeze them. Place the cooled cookies on a tray to freeze solid, then transfer to freezer bags. Press out the air and label the date. They keep nicely for up to 2 months. When you’re craving a bright bite, thaw a couple on the counter for 30 minutes. If you want them a touch warm, a quick 10-second microwave burst perks them up.
Thawing Without Sogginess
Moisture is the enemy of shine. Thaw at room temperature on a wire rack so any condensation escapes. If tops look damp after thawing, a few minutes in a low oven helps revive the caramel sheen.
By the way, if you want a gentle refresher on portioning and baking times for consistent texture, consider practicing with a classic base like the perfect soft chocolate chip cookies. The same don’t-overbake rule applies here, too.
Substitutions & Variations
Flavor riffs
Use pineapple tidbits for a rustic look or half rings to fit neatly. Fresh pineapple works if you cut it thin and pat it dry, but canned is usually easier and more dependable for size and moisture.
Swap vanilla for almond extract to echo that old-school bakery vibe. A light dusting of cinnamon in the brown sugar layer adds warmth that plays well with pineapple. For a beachy twist, mix a teaspoon of coconut flakes into each muffin cup before the pineapple. The coconut toasts as the cookies bake and adds a little chew.
If you want to speed things up, you can shortcut the dough with a cake mix base. This tutorial helps you understand how cake mixes behave in cookie form: cake mix cookies. Just remember, you still need the brown sugar and pineapple layer in the muffin cups to get that signature flip and gloss.
Feeling adventurous? Add a tiny splash of rum extract to the dough for a playful tropical note. Or sprinkle a pinch of flaky salt on top after flipping to balance the sweetness.
Pro Tips
- Butter and sugar basics: Cream butter and sugar long enough to look slightly fluffy. This keeps the cookie layer soft and tender.
- Dry your fruit: Blot pineapple and cherries. Less moisture equals prettier tops and better caramel.
- Don’t overfill: Too much brown sugar can cause a syrupy overflow that sticks. A teaspoon per cup is plenty.
- Flip while warm: Give the pan a 2 to 3 minute rest, then flip. Too soon and the caramel can run. Too late and it can set like glue.
- Pan matters: A light-colored muffin tin reduces over-browning. Dark pans cook faster at the edges, so check early.
- Practice timing: Pull cookies when the edges are just golden. A minute too long and they dry out.
- Make it a menu: Serve these after a casual grilled dinner or pair them with something tropical. I love them after Hawaiian BBQ chicken and pineapple foil packets for a full island-inspired meal.
Common Questions
Why are my cookies sticking to the pan? Most likely the caramel set too hard or the pan was not greased enough. Loosen the edges with a thin knife, warm the bottom of the pan briefly with a hot towel, and try flipping again.
Can I make the dough ahead of time? Yes. Chill the dough up to 48 hours. Let it soften slightly so you can press it over the fruit without cracking.
Do I have to use cherries? No. They’re classic, but you can skip them or swap in a tiny dab of jam for color. Raspberry or apricot both work well.
How do I keep the tops glossy? Dry your fruit, measure the brown sugar lightly, and flip while the cookies are still warm. Cooling on a wire rack helps moisture escape.
Can I make these without a muffin tin? You can try a mini tart pan with removable bottoms, but a muffin tin really gives the right shape and holds the caramel in place.
Ready to Bake and Share Some Sunshine
If you love the idea of a little cake in cookie form, these Pineapple Upside Down Sugar Cookies deliver big flavor in a small package. The brown sugar caramel, juicy pineapple, and soft sugar cookie make a great team. For more inspiration, check out this detailed take on the technique in Pineapple Upside Down Sugar Cookies – Cookie Dough and Oven …, or try the bright and simple method from Easy Pineapple Upside Down Sugar Cookies Recipe. Gather your ingredients, preheat the oven, and get ready for that satisfying flip. Your kitchen is about to smell amazing, and your plate will look even better.