Pineapple Upside-Down Sugar Cookies

Picture a tray of buttery, golden cookies crowned with glossy caramel, ruby cherries, and sunlit pineapple—edges delicately crisp, centers soft and tender, the air warm with brown sugar and tropical vanilla.

Imagine lifting one while it’s still just-warm, the caramel sheen catching the light and the first bite delivering tangy pineapple against a melt-in-your-mouth sugar cookie—comfort and celebration in two bites.

I love how these tiny upside-down beauties distill the nostalgia of the classic cake into weeknight-manageable treats; they look special without fuss and perfume the kitchen like a bakery.

They’re perfect for busy weeknights or Sunday suppers, potlucks where you need a grab-and-go dessert, or that moment when you promised something “homemade” and time shrank.

Once, these cookies saved my nephew’s birthday after the cake sagged; twenty minutes later, we’d a platter of jewel-topped smiles.

Ready? Let’s cook!

Why You’ll Love It

• Delivers bright, caramelized pineapple flavor in every bite
• Bakes fast in muffin pans for tidy, mini treats
• Balances soft centers with lightly crisp, golden edges
• Uses simple pantry staples plus canned pineapple and cherries
• Releases cleanly when fruit is well-dried and topping glossy

Ingredients

• 113 g unsalted butter, softened — room temp for easy creaming
• 150 g granulated sugar — fine granules dissolve evenly
• 50 g light brown sugar, packed — adds moisture and caramel notes
• 1 large egg, room temperature — blends better into batter
• 1 tsp vanilla extract — pure vanilla for best flavor
• 180 g all-purpose flour — measure accurately to avoid dryness
• 1/2 tsp baking powder — check freshness for proper lift
• 1/4 tsp baking soda — balances acidity of juice
• 1/4 tsp fine salt — enhances overall flavor
• 60 ml pineapple juice, room temperature — not from concentrate if possible
• 42 g unsalted butter, for topping — melts smoothly for caramel
• 100 g light brown sugar, for topping — creates glossy syrup
• 12 maraschino cherries, halved — drain well to prevent sogginess
• 1 can (398 ml) pineapple rings, drained and patted dry — choose firm rings for clean cuts

Step-by-Step Method

Preheat & Prepare Pans

Preheat oven to 350°F (175°C). Lightly grease two standard 12-cup muffin pans. Set a wire rack nearby for inverting later. Gather all tools and ingredients to streamline the process. Pat pineapple rings and cherries very dry with paper towels. This prevents soggy tops and helps clean release after baking.

Cook the Caramel Topping

Melt 42 g unsalted butter in a medium saucepan over medium heat. Whisk in 100 g light brown sugar. Simmer about 30 seconds until glossy and smooth. Remove from heat.

If it thickens while portioning, briefly rewarm to keep it pourable and easy to distribute into muffin cups.

Portion the Topping

Divide the warm brown sugar-butter mixture among 24 muffin cups. Aim for about 1 teaspoon per cup. Use a small spoon or pastry brush to spread it evenly across the bottom. Work quickly so it doesn’t set.

Even coverage promotes a uniform caramel layer on the finished cookies.

Cut & Place the Fruit

Cut pineapple rings into small wedges to fit the muffin cups. Trim for a flat fit and pat dry again. Place one pineapple wedge and one maraschino cherry half, cut-sides down, into each sugared cup.

Assure they sit flat to avoid bulging and to help the cookies invert cleanly later.

Cream Butter & Sugars

In a large mixing bowl, beat 113 g softened butter with 150 g granulated sugar and 50 g light brown sugar. Use a stand mixer or hand mixer. Beat on medium speed for 2 to 3 minutes until light and fluffy. Scrape the bowl as needed.

Proper aeration creates tender, soft cookie centers.

Add Egg & Vanilla

Beat in 1 large room-temperature egg and 1 teaspoon vanilla extract. Mix until smooth and fully combined. Don’t overmix. Scrape down the bowl to incorporate any streaks.

The mixture should look creamy and slightly thick, with no visible egg bits or separation.

Whisk Dry Ingredients

In a separate bowl, whisk 180 g all-purpose flour, 1/2 teaspoon baking powder, 1/4 teaspoon baking soda, and 1/4 teaspoon fine salt. Break up any lumps. Even distribution of leaveners ensures consistent lift.

Keep this bowl nearby to incorporate in stages with the wet mixture.

Combine Wet & Dry

Add half the dry ingredients to the butter mixture. Mix on low just until nearly combined. Stream in 60 ml pineapple juice and blend briefly.

Add remaining dry ingredients and mix until just combined. Avoid overmixing. A tender dough helps the cookies stay soft with defined edges.

Portion the Dough

Use a 1.5-tablespoon cookie scoop to portion dough. Place one level scoop over the fruit in each muffin cup. Gently press to fill the surface evenly without compacting.

Ensure edges reach the sides for a neat round shape. Even portions bake uniformly and release more easily.

Bake to Set

Bake 10 to 12 minutes until edges are lightly golden and centers are just set. Avoid overbaking to keep the middles soft. Rotate pans halfway if your oven has hot spots.

Look for slight spring when touched and minimal gloss on the surface for perfect texture.

Cool Briefly in Pan

Let cookies cool in the pans for 5 minutes. This allows the caramel to set just enough to release without tearing. Don’t wait too long or the topping may stick firmly.

Prepare your cooling rack for a swift, smooth inversion when the five-minute rest ends.

Loosen & Invert

Run a thin knife around each cookie to loosen the edges. Invert the pan over a wire rack and lift carefully to release the cookies.

If any fruit or caramel sticks in the cup, spoon it back onto the warm cookie immediately. Let cookies cool an additional 15 minutes before serving.

Ingredient Swaps

• Dairy-free: Use vegan butter for both dough and topping; check that sugar is vegan.
• Gluten-free: Substitute a 1:1 gluten-free all-purpose blend; add 1–2 tsp milk or juice if dough seems dry.
• Egg-free: Replace 1 egg with 3 tbsp aquafaba or a flax egg (1 tbsp ground flax + 3 tbsp water, rested 5 min).
• Lower refined sugar: Use coconut sugar in dough and topping (caramel will be slightly less glossy).
• Budget/availability: Use canned crushed pineapple (very well-drained) instead of rings; jarred or frozen cherries in place of maraschino.
• Flavor swaps: Orange or mango juice for pineapple juice; add 1/2 tsp rum extract or cinnamon to the topping.
• Nutty twist: Fold in 30–45 g finely chopped toasted pecans into the topping before portioning.

You Must Know

Doneness • If edges look pale and centers feel glossy-wet, leave them 1–2 minutes longer; pull when edges are lightly golden and the centers spring back with a gentle tap—carryover heat finishes setting in about 5 minutes.

Troubleshoot • If cookies won’t release cleanly, return the pan to the warm (off) oven for 1 minute, then invert again; gentle warmth remelts the sugar layer so it loosens—look for a glossy, fluid sheen before flipping.

Avoid • Avoid juicy fruit: press pineapple between double paper towels with a light hand for 10–15 seconds per piece; excess moisture dilutes the 100 g sugar-butter glaze, causing grainy tops and stuck fruit.

Scale • For 12 cookies, use half quantities (e.g., 90 g flour, 30 ml juice, 56 g butter in dough, 21 g butter + 50 g brown sugar for topping) and portion ~1.5 tbsp dough per cup; timing stays within 10–12 minutes—start checking at 9.

Flavor Boost • For deeper caramel notes, sprinkle a tiny pinch (about 1/16 tsp) flaky salt over each cup right after inversion, or add 1/4 tsp rum extract to the dough; the salt sharpens sweetness and the rum evokes classic pineapple-upside-down cake.

Serving Tips

• Serve warm with a scoop of vanilla bean ice cream or coconut gelato.
• Garnish with toasted shredded coconut and a drizzle of caramel sauce.
• Plate on banana leaves or small dessert plates with a lime zest sprinkle.
• Pair with sparkling pineapple mocktail or a light Riesling.
• Add a dollop of lightly sweetened whipped cream and a mint sprig.

Storage & Make-Ahead

Store cookies airtight in the fridge up to 5 days.

Rewarm 10–15 seconds to refresh the caramel gloss.

Make the dough 2 days ahead and chill.

Or portion and refrigerate filled pans up to 12 hours before baking.

Baked cookies freeze well for 2 months.

Thaw at room temperature.

Reheating

Reheat gently: microwave 1–2 cookies 8–12 seconds.

Oven: 300°F (150°C) for 4–6 minutes on a sheet.

Stovetop: covered skillet on low 2–3 minutes.

Avoid overbaking; aim just warmed.

County-Fair Blue Ribbon

Once they’re gently warmed and glossy again, I’m ready to think like a judge and bake these cookies for a blue ribbon. At the fair, first impressions matter: I aim for uniform size, even caramel, and a bright cherry wink in every cup. I pat the pineapple dry until it squeaks, then trim neat wedges so they sit flat and release cleanly.

I cream butter and sugars until airy, no graininess, then stop mixing the flour the moment it disappears—tender beats tough. I portion with a level scoop, press lightly to seal the fruit, and bake until edges just kiss gold.

For transport, I layer parchment between rows, then rewarm 10 seconds before judging. The result? Glossy tops, buttery crumb, citrusy perfume—pure ribbon magnet.

Final Thoughts

Ready to bake a little sunshine? Give these Pineapple Upside-Down Sugar Cookies a try, and feel free to tweak the toppings—add a pinch of cinnamon, swap in crushed pineapple, or play with extra cherries to make them your own!

Frequently Asked Questions

Can I Make These Gluten-Free Without Gritty Texture?

Yes—use a quality 1:1 gluten‑free flour blend with xanthan gum, plus 10% extra by weight. I whisk in 1 tablespoon cornstarch, rest the dough 20 minutes, and don’t overbake. The result: tender, non‑gritty, caramel‑kissed bliss.

How Do I Prevent Sticking in Silicone Muffin Pans?

Grease silicone wells lightly, then spoon in warm butter-brown sugar first. I pat fruit bone-dry, add a pinch of salt to the caramel, scoop dough gently, and cool five minutes before inverting. Stuck bits? I spoon them back.

What Altitude Adjustments Are Needed for Dough and Bake Time?

At high altitudes, I add 2–3 tablespoons flour, reduce sugar slightly, and increase pineapple juice a touch. I bake hotter—365°F—and shorten time 1–2 minutes, watching edges set and centers softly puff before pulling.

Can I Freeze Unbaked Dough Already Portioned in Cups?

Yes—you can freeze them. I portion the dough into lined cups, freeze solid, then pop into bags. Bake from frozen, adding 2–4 minutes. Freeze the fruit-topped sugar base separately to keep caramel glossy and release cleanly.

How Do I Scale the Recipe for a Mini Muffin Pan?

Use the recipe as-is; it yields 48 minis. I cut pineapple smaller, use 1 teaspoon caramel and a level 2-teaspoon dough scoop per cup. Bake 8–9 minutes, rotate once, then invert quickly—tiny crowns gleam like sunset jewels.