Why You'll Love It
- - Simple ingredients you probably already have
- - Soft, buttery texture with a caramelized fruit topping
- - Quick to bake, perfect for spontaneous cravings
- - A nostalgic nod to classic upside‑down desserts
*"These cookies taste like a warm hug with a tropical twist—my kids can’t get enough!"*
Essential Ingredient Guide
- Pineapple rings: Choose fresh or canned rings; pat dry to avoid soggy tops.
- Unsalted butter: Room‑temperature butter creates a tender crumb.
- Brown sugar: Adds depth and helps caramelize the fruit.
- Vanilla extract: A splash brightens the overall flavor.
- Lemon juice: A tiny dash balances sweetness with a subtle zing.
- All‑purpose flour: Provides structure; sift for a lighter dough.
Complete Cooking Process
-
Ingredient Readiness:
Measure and soften butter, drain pineapple, and preheat the oven.
-
Flavor Development:
Caramelize brown sugar with butter, then nest pineapple rings.
-
Texture Control:
Mix dough just until combined to keep cookies soft.
-
Finishing Touches:
Press dough over fruit, bake until golden, then cool on a rack.
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Serving Timing:
Serve warm or at room temperature for the best texture.
- Chill the dough for 15 minutes for cleaner shapes
- Use a cookie scoop for even sizing
- Rotate the pan halfway through baking for even color
- Let cookies rest briefly before removing to set the caramel
Pro Tips
Well, those little tricks can make a big difference. I’ve found that chilling the dough not only helps the cookies keep their shape, but also gives the butter a chance to firm up, so the caramel stays glossy. Also, when you let them cool just a touch before moving them, the fruit’s glaze holds together better, making each bite look as lovely as it tastes. So, take a moment, enjoy the aroma, and let the kitchen settle into a calm rhythm.
The essence of the dish:
A fun fact or historical angle:
Flavor or sensory focus:
You Must Know
- Do not over‑mix the dough
- Press the dough gently over the fruit
- Cool on a wire rack for crisp edges
Frequently Asked Questions
→ Can I use fresh pineapple instead of canned?
Yes, fresh rings work beautifully; just pat them dry and slice thinly for even caramelization.
→ Do I need to chill the dough?
Chilling for 15 minutes helps keep the cookies’ shape and yields a softer crumb.
→ Can I make these gluten‑free?
Swap all‑purpose flour for a 1‑to‑1 gluten‑free flour blend; the texture remains tender.
→ How long can I store the cookies?
Keep in an airtight container at room temperature for up to three days; they stay moist.
→ What if I want a spicier version?
Add a pinch of ground ginger or a few drops of vanilla‑infused rum for warmth.
→ Can I freeze the baked cookies?
Yes, freeze in a single layer, then transfer to a bag; re‑heat gently before serving.
Chef's Tips
If the caramel hardens before baking, gently warm the sheet for a minute.,For extra sparkle, brush the tops with a light glaze of apricot jam after cooling.,Use a cookie scoop for uniform size and even baking.
Nutrition Facts
per serving
210
Calories
2g
Protein
30g
Carbs
9g
Fat
Taste Profile
Buttery sweetness with bright tropical notes
Ingredient Substitutions
Don't have an ingredient? Try these alternatives
Will give a nuttier flavor and denser crumb.
Adds a caramel note with a lower glycemic index.
Recipe Variations
Try these delicious twists on the original
Spicy Version
Add a pinch of ground ginger and a dash of cayenne for a warm kick.
Mediterranean Style
Mix in crumbled feta and a few olives for a savory twist.
Common Mistakes to Avoid
Learn from others' mistakes for perfect results
- Over‑mixing the dough, which makes cookies tough
- Adding pineapple before the caramel has softened, leading to soggy tops
- Baking too long, causing the caramel to harden
Meal Prep & Storage
Make Ahead Tips
You can prepare the dough up to 24 hours ahead; keep chilled and shape just before baking.
Leftover Ideas
Reheat gently in a skillet over low heat to revive the caramel glaze.
Perfect Pairings
Serve this with...
Cooking Timeline
Gather all ingredients, soften butter, and preheat oven.
Cream butter with sugars, add egg, vanilla, and lemon juice.
Fold in dry ingredients, chill dough if needed.
Prepare caramel topping, place pineapple rings, and form dough around them.
Bake, cool slightly, then transfer to rack.
Pineapple Upside Down Sugar Cookies – Easy Recipe
Enjoy sweet pineapple upside down sugar cookies with caramelized fruit and buttery crumbs – a perfect cozy treat that feels like sunshine on a rainy day.
Timing
Prep Time
20 Minutes
Cook Time
15 Minutes
Total Time
35 Minutes
Recipe Details
Ingredients
Main Ingredients
- 01 1 cup unsalted butter, softened
- 02 1/2 cup brown sugar, packed
- 03 1/2 cup granulated sugar
- 04 1 large egg
- 05 1 teaspoon vanilla extract
- 06 2 cups all‑purpose flour
- 07 1/2 teaspoon baking powder
- 08 1/4 teaspoon salt
- 09 1 tablespoon lemon juice
For the Topping
- 01 1 can pineapple rings, drained
- 02 2 tablespoons brown sugar
- 03 1 tablespoon butter, melted
Instructions
Preheat the oven to 350°F (175°C) and line a baking sheet with parchment.
In a bowl, cream softened butter with brown and granulated sugar until light and fluffy.
Add the egg, vanilla, and lemon juice; mix until just combined.
Whisk flour, baking powder, and salt; fold into the wet mixture, handling gently.
In a small saucepan, combine melted butter and 2 Tbsp brown sugar; heat until bubbling, then remove from heat.
Place a pineapple ring on the prepared sheet, spoon a little caramel sauce over it, then press a spoonful of dough around the ring, flattening gently.
Repeat for remaining rings, spacing evenly; bake 12‑14 minutes until edges are golden.
Cool on the sheet briefly, then transfer to a wire rack; enjoy warm, perhaps with a cup of tea.
Notes & Tips
- 1 If the caramel hardens before baking, gently warm the sheet for a minute.
- 2 For extra sparkle, brush the tops with a light glaze of apricot jam after cooling.
- 3 Use a cookie scoop for uniform size and even baking.
Tools You'll Need
-
Mixing bowls
-
Hand mixer or whisk
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Baking sheet
-
Parchment paper
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Spatula
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Small saucepan
Must-Know Tips
- Don’t over‑mix the dough; it keeps cookies tender
- Chill the dough if it feels sticky
- Rotate the pan halfway for even caramel color
Professional Secrets
- Room‑temperature butter mixes evenly without over‑working the flour
- Caramelizing sugar briefly adds depth without burning
- Cooling on a wire rack preserves the glossy finish
Recipe by
Mason Cole“Sweet cravings are my specialty! I turn sugar, chocolate, and imagination into pure dessert magic.” 🍰✨
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