Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies take everything you love about the classic pineapple upside down cake and wrap it into a buttery soft cookie. These are perfect for parties or when you just need a splash of tropical flair in the middle of your week.

I started making these after my mom requested her two favorite desserts in one bite and now they are requested at every summer picnic. Last time I made these for friends our kitchen smelled like caramel and sunshine and everyone went home asking for the recipe.

Ingredients

• Butter at room temperature: gives your cookies that irresistible tenderness and carries the caramel notes
• Granulated sugar: for classic sweetness and that soft chew
• Eggs: for binding everything together and adding richness
• Vanilla extract: brings depth and aroma go for pure extract for the best flavor
• Sour cream: adds moisture and a tender crumb use full fat for the creamiest result
• All purpose flour: for that sturdy but soft cookie foundation choose unbleached for a more delicate texture
• Baking powder: ensures lift and fluffiness check that it is fresh for the best result
• Cornstarch: keeps the cookie crumb tender and helps prevent spreading
• Salt: heightens the flavors and balances sweetness opt for fine sea salt if possible
• Canned pineapple slices: bring brightness and tropical zest look for firm rings without blemishes
• Maraschino cherries: add that signature sweet pop and an eye catching finish
• Melted butter mixed with brown sugar: becomes the sticky caramel base use fresh light brown sugar and quality butter for a glossy finish

Instructions

Prep the Pan:

Generously coat a mini round cake pan with nonstick spray making sure each cavity is well greased for easy release

Cream the Butter and Sugar:

Beat room temperature butter with granulated sugar on medium speed until pale and fluffy this usually takes at least 3 minutes and ensures that signature cookie lightness

Add Wet Ingredients:

Mix in eggs one at a time followed by vanilla extract and sour cream Beat at low speed until just blended to avoid overmixing

Combine Dry Ingredients:

In a separate bowl whisk together flour baking powder cornstarch and salt Make sure they are evenly mixed to guarantee even rise and crumb

Form the Dough:

Stir the dry ingredients into the wet mixture slowly using a spoon or mixer on low just until a soft dough forms You should see no streaks of flour

Make the Caramel Base:

In another bowl mix melted butter with packed brown sugar until smooth and glossy This layer delivers the signature sticky top

Assemble Each Cookie:

Spoon about 1 tablespoon of the butter brown sugar mixture into each prepared pan cavity press a pineapple slice in and nestle a maraschino cherry in the center

Portion and Top with Dough:

Scoop about 3 tablespoons of dough over each pineapple gently pressing to cover and flatten a bit creating a seal for gooey caramel

Bake to Perfection:

Bake at 350 degrees Fahrenheit for about 25 minutes until the edges are deep golden the top is set and you can see the sugar bubbling

Cool and Invert:

Let cookies sit in the pan for 10 minutes then carefully invert onto wax paper If any pineapple gets left behind just gently reposition it while still warm

Finish and Store:

Allow cookies to cool completely before serving Store in an airtight container at room temperature for up to three days

When I pop a maraschino cherry in the middle of the pineapple it always brings back memories of my grandma tucking cherries into her cakes as a Sunday treat. The touch of browned butter and caramelized sugar is by far my favorite part.

Storage Tips

Keep these cookies in an airtight container at room temperature They will stay soft and moist for up to three days. For longer storage pop them in the refrigerator but let them come to room temperature before serving so the caramel can soften again

Ingredient Substitutions

You can use Greek yogurt instead of sour cream for a similar tender crumb. If you do not have mini round cake pans a muffin tin will work just fine though the shape might be a bit deeper. Dough can handle chopped pecans or coconut for added texture

Serving Suggestions

These cookies are a showstopper all on their own but they also shine as a dessert platter centerpiece. Serve with a scoop of coconut ice cream for a truly tropical finish or drizzle with a touch of rum caramel for adults.

Cultural and Historical Context

Pineapple upside down cakes became popular in the early twentieth century as canned pineapple became widely available. These cookies are a nod to that vintage tradition recast for bite sized fun and modern gatherings. The cherry in the middle is a classic throwback and always sparks nostalgia at the table.

Seasonal Adaptations

Substitute fresh pineapple for canned when it is in season for even brighter flavor Add a sprinkle of cinnamon or nutmeg in the winter for cozy warmth Try diced mango or peach rings in place of pineapple to celebrate summer’s bounty

Success Stories

The first time I made these they disappeared before the rest of dinner could get on the table. They are especially popular with kids since everyone gets their own little cake. Friends often text me later to say they made a batch for family game night or a neighborhood barbecue.

Freezer Meal Conversion

Prepare cookies as directed and allow them to cool completely. Freeze in a single layer then transfer to containers with parchment between layers. Thaw at room temperature for a quick make ahead dessert that still tastes freshly baked.

These cookies bring a splash of sunshine and nostalgia to any gathering. Enjoy them fresh with family or store for later to savor that caramel goodness all week long.

Recipe FAQs

→ How do you achieve the upside-down effect?

Layer pineapple slices, a cherry, and brown sugar mixture at the bottom of each pan cavity before adding the dough. After baking, invert the cookies so fruit tops each one.

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple slices work well if cut to fit the pan. Ensure they are well-drained to prevent excess moisture.

→ Why use sour cream in the dough?

Sour cream adds moisture and tenderizes the cookie, resulting in a softer, richer crumb.

→ How do I prevent the cookies from sticking?

Let the cookies cool in the pan for 10 minutes before inverting. If fruit sticks, gently reposition on top while still warm.

→ How should these cookies be stored?

Keep cookies in an airtight container at room temperature. For the best texture, enjoy within 2–3 days of baking.