Pineapple Upside Down Sugar Cookies

Nothing says summer fun like a batch of pineapple upside down sugar cookies They combine a super soft and fluffy sugar cookie with juicy caramelized pineapple and a cherry on top One bite and I am instantly transported back to childhood picnics and sunny afternoons with family

I still remember surprising my family with these on a hot July day The cookies were gone before the lemonade was finished and now they are a permanent request for every reunion

Ingredients

• Butter: Use top quality butter for best flavor and texture I always let mine soften at room temperature so it creams perfectly with sugar
• Granulated sugar: Gives the cookie its soft sweetness Organic or premium brands melt smoothly
• Eggs: Needed for richness and binding I choose large farm fresh eggs whenever possible for best results
• Vanilla extract: Adds fragrant warmth Real vanilla brings more depth than imitation
• Sour cream: Keeps the cookie extra moist and tender Look for full fat for that bakery softness
• All purpose flour: The backbone of the cookie Always spoon and level it to avoid dense cookies
• Baking powder: Helps the cookies puff up beautifully
• Cornstarch: Makes the crumb extra soft and melt in your mouth
• Salt: Balances the sweetness so flavors shine
• Canned pineapple slices: Juicy topping for each cookie Choose rings in juice not syrup and pat them dry for best texture
• Maraschino cherries: Classic center accent for color and a pop of flavor Look for bright red cherries packed in juice for a fresher taste
• Light brown sugar: Brings caramel notes under the fruit Press lightly into measuring cup to pack it gently
• Butter: Melted for a rich caramel base that bubbles up with the sugar

Step by Step Instructions

Make the Sugar Cookie Dough:

Cream room temperature butter and sugar together in a large mixing bowl until very light and fluffy This should take about three minutes and is essential for a soft texture

Mix in Wet Ingredients:

Blend in eggs vanilla extract and sour cream Make sure to scrape down the bowl so everything is evenly combined

Add Dry Ingredients:

Stir in flour baking powder cornstarch and salt Sift ahead if your flour is lumpy Gently mix just until the dough comes together to avoid tough cookies

Make the Brown Sugar Caramel:

In a separate bowl combine melted butter and brown sugar Stir thoroughly until fully blended and smooth

Assemble Cookies in Pan:

Spoon about one tablespoon of the brown sugar mixture into the bottom of each mini cake pan cavity Use a spoon to spread it evenly across the base

Add Fruit Topping:

Place one pineapple ring on top of the brown sugar layer Gently push a maraschino cherry into the center hole of each ring

Top with Cookie Dough:

Drop a scoop of cookie dough over the fruit about three tablespoons per cookie Use an offset spatula or spoon to spread the dough flat so it completely covers the fruit

Bake the Cookies:

Bake at 350 degrees for about 25 minutes until edges are golden and caramel is bubbling on the sides Be patient for caramelization to happen as this gives the cookies their signature look

Cool and Remove from Pan:

Let cookies sit in the pan for ten minutes to set up carefully loosen with a spatula and turn out onto wax paper The caramel will run so wax paper is important for easy clean up

Rescue Toppings if Needed:

If any pineapple or cherry sticks to the pan simply place it carefully back on top of the cookie while still warm

Cool Completely:

Let the cookies finish cooling before serving or storing so the caramel sets and flavors meld

My favorite ingredient here is the brown sugar caramel because it turns gooey and almost candy like under the fruit I love seeing my kids sneak the first sizzling cookies off the tray and hearing the laughter about whose cherry ended up in Dad’s cookie

Storage Tips

Once cooled store cookies in an airtight container at room temperature for up to three days Since the pineapple adds moisture I always put a layer of wax or parchment paper between layers to prevent sticking If you are saving them longer chill them in the fridge and bring back to room temperature before serving

Ingredient Substitutions

If you cannot find canned pineapple rings try fresh pineapple cut in thick slices and cored to size You can also swap maraschino cherries for glacé cherries or even use slices of kiwi for a tropical spin For extra vanilla flavor try using vanilla bean paste in the dough

Serving Suggestions

These cookies are perfect served slightly warm with a scoop of vanilla ice cream for a quick dessert They make a fun centerpiece at any summer barbecue or picnic I sometimes set out bowls of whipped cream and toasted coconut for a build your own sundae bar with these cookies as the base

Cultural and Historical Context

Pineapple upside down cakes first became popular in the early twentieth century when canned pineapple became widely available The upside down presentation made home bakers feel like professional pastry chefs These cookies are a modern playful twist bringing the same nostalgic flavors into an everyday treat

FAQs about Recipes

→ How do I prevent the pineapple from sticking to the pan?

Ensure the pan is well-greased and use wax paper for easy removal. If the pineapple sticks, gently reposition it after turning out.

→ Can I use fresh pineapple instead of canned?

Fresh pineapple works well. Slice thinly and pat dry to prevent excess moisture during baking.

→ How should I store these cookies?

Store in an airtight container at room temperature for up to three days to maintain softness and flavor.

→ Is it necessary to use a mini cake pan?

Mini cake pans help achieve the signature upside down look, but muffin tins or ramekins may be substituted.

→ Can I make these ahead of time?

Yes, they are best enjoyed within two to three days. Prepare and store tightly covered for freshness.