Why this recipe works

This recipe balances structure and moisture: a rich butter-sugar cookie provides a sturdy,
soft base while a small “caramel” pocket (brown sugar + melted butter) beneath each
pineapple ring melts into the fruit during baking and creates the shiny, caramelized
finish when the cookie is inverted. Using a muffin tin keeps the final cookie tall and
cake-like — perfect for presentation and portion control.

Pro tip: Dry the canned pineapple very well so the caramel layer doesn’t become too thin or runny during baking.

Ingredients & what each one does

Cookie dough

• 1 cup unsalted butter (softened) — creates a rich, tender cookie base and helps deliver a soft, chewy interior.
• 1 cup granulated sugar — sweetens and helps produce lightly crisp edges while keeping the center tender.
• 1 large egg — binds the dough and gives the cookie structure and moisture.
• 2 teaspoons vanilla extract — deepens and rounds the flavor; pairs beautifully with the pineapple topping.
• 2½ cups all-purpose flour — forms the cookie’s structure while keeping the texture thick and soft.
• 1 teaspoon baking powder — adds a gentle lift so cookies are soft and slightly fluffy.

Caramel and topping

• ½ cup brown sugar — creates the caramelized layer beneath the pineapple; its molasses notes complement the fruit and cookie.
• ¼ cup melted butter — helps the brown sugar turn into a sticky caramel and prevents sticking to the pan.
• 12 pineapple rings (drained & patted dry) — delivers juicy tropical flavor; patting dry prevents excess liquid from thinning the caramel.
• 12 maraschino cherries — the classic visual and flavor pop in the center of each ring.

Equipment

• 12-cup muffin pan (metal recommended for best caramelization)
• Mixing bowls
• Hand mixer or stand mixer
• Measuring cups & spoons
• Spoon or small cookie scoop (for portioning dough)
• Paper liners or parchment rounds (optional)

How to make Pineapple Upside Sugar Cookies — Detailed, step-by-step

1. Preheat & prepare pans: Preheat the oven to 350°F (175°C).
   Grease a 12-cup muffin pan well with butter or nonstick spray. For easiest removal,
   you can use parchment rounds in each cup or lightly butter the sides and bottom.
2. Make the caramel base: In a small bowl combine ½ cup brown sugar
   and ¼ cup melted butter. Stir until the mixture is evenly moistened and looks
   like damp sand. Spoon about a heaping teaspoon of this mixture into the bottom of each
   muffin cup, spreading it into a thin, even layer.
3. Place pineapple & cherry: Place one pineapple ring on top of the brown-sugar
   mixture in each cup. Press gently so it sits level. Drop one maraschino cherry into the
   center hole of each pineapple ring. If rings are larger than the cups, trim to fit.
4. Make the cookie dough — step A: cream the butter & sugar: In a large bowl,
   cream 1 cup softened butter with 1 cup granulated sugar until
   light and fluffy (about 3–4 minutes with a mixer). Scrape the bowl as needed.
5. Cookie dough — step B: add egg & vanilla: Beat in the 1 large egg
   until incorporated, then mix in 2 teaspoons vanilla extract.
6. Cookie dough — step C: combine dry ingredients: In a separate bowl, whisk together
   2½ cups all-purpose flour and 1 teaspoon baking powder. Gradually
   add the dry mixture to the wet mixture and stir just until combined. The dough should be soft
   yet hold its shape when scooped.
7. Portion the dough: Using a small scoop or tablespoon, place about 2–3 tablespoons
   of cookie dough over each pineapple ring, gently flattening the top so the dough reaches
   near the rim but does not overfill (cookies will rise slightly).
8. Bake: Bake on the center rack for 16–20 minutes, or until the
   cookie tops are set and the edges are light golden. The caramel beneath will bubble slightly.
   Oven times vary; check at 14 minutes and judge by appearance.
9. Cool & invert: Allow the pan to cool for 5–7 minutes (don’t wait until completely
   cold). Run a small knife around each cup to loosen edges. Place a serving plate or rack over
   the muffin tin and carefully invert the pan. Gently lift the tin — the cookies should release,
   revealing glossy caramelized pineapple rings with cherries in the center.
10. Final touch: If any caramel stuck to the pan, spoon it back onto the cookie tops.
    Cool to warm or room temperature before serving.

Pro tips & tricks for consistently great results

• Dry the pineapple thoroughly: Excess juice will thin the caramel and produce a runny base.
• Use metal muffin pans: They brown and caramelize better than silicone, giving that glossy finish.
• Room-temperature butter: Softened (not melted) butter helps cream properly with sugar, creating lighter cookies.
• Don’t overwork the dough: Mix until just combined to keep a tender crumb.
• Even portions: Use a cookie scoop for uniform cookies so they bake evenly and invert nicely.
• Timing for inversion: Invert while the caramel is warm but the cookies are cool enough to hold their shape — about 5–7 minutes.
• Make ahead: You can assemble in the muffin pan and refrigerate (covered) for a few hours; bake from cold but add a minute or two to baking time.

Creative variations & flavor ideas

• Coconut Tropics: Fold ¼ cup sweetened shredded coconut into the dough and sprinkle toasted coconut on top after inverting.
• Brown Butter Boost: Use browned butter in the dough for nutty caramel notes that pair perfectly with pineapple.
• Pineapple-Lemon: Add 1 tsp lemon zest to the dough for bright, citrus complexity.
• Chocolate Drizzle: Drizzle melted white or dark chocolate over cooled cookies for contrast and decoration.
• Mini Upside-Down Cakes: Double the dough and bake in jumbo muffin tins for larger single-serving cakes.

Serving & presentation ideas

These cookies are delightful warm, at room temperature, or gently reheated.

• Serve warm with a scoop of vanilla ice cream for an instant dessert.
• Arrange on a platter with mint sprigs or a dusting of powdered sugar for a polished look.
• Offer alongside coffee or tea at brunch — their fruity brightness balances rich beverages.

Storage & make-ahead

Store leftovers in an airtight container at room temperature for up to 3 days.
Refrigerate up to 1 week — allow to come to room temperature or warm 6–8 seconds
in the microwave before serving. For longer storage, freeze cooled cookies in a single layer
separated by parchment paper for up to 2 months; thaw overnight in the fridge.

Common mistakes & how to fix them

• Caramel too thin or pooling: You likely used too-wet pineapple. Pat pineapple rings dry and reduce the brown sugar slightly if needed.
• Cookies stick to pan when inverted: Make sure you greased the pan well, and invert while still warm (not hot or fully cold).
• Flat cookies: Overworked dough or melted butter in the dough can cause excess spreading. Use softened (not melted) butter and mix just until combined.
• Uneven baking: Use uniform dough portions and rotate the pan halfway through baking for ovens with hot spots.