Pineapple Upside Sugar Cookies: A Perfect Treat5🍍🍍🍍

Pineapple Upside Sugar Cookies: Sweet & Irresistible

If you’re a fan of classic pineapple upside-down cake and soft, buttery sugar cookies, these Pineapple Upside-Down Sugar Cookies are a dream come true. Combining the nostalgic charm of a tropical cake with the irresistible texture of a cookie, this dessert is a fun and delicious twist on two favorites. These cookies are baked in muffin tins, creating individual portions that are both beautiful and easy to serve.

At the base (which becomes the top when flipped), you get a caramelized layer of melted butter and brown sugar, perfectly soaking into a slice of pineapple and a bright maraschino cherry. This creates a glossy, golden topping that’s sweet, sticky, and visually stunning. Beneath that tropical crown lies a soft and chewy sugar cookie—rich, buttery, and just the right amount of sweet to balance the fruity topping.

These cookies are perfect for summer gatherings, potlucks, bake sales, or even holiday cookie trays when you want to offer something a little unexpected. They’re easy to make with pantry staples and a can of pineapple rings, and they look far more impressive than the effort required. Serve them warm for gooey indulgence, or let them cool for a firmer, more cookie-like bite. Either way, they’re guaranteed to be a crowd-pleaser!

📌 Number of Servings: Makes 12 cookies

⏳ Preparation Time: 20 minutes

🔥 Cooking Time: 15–18 minutes

🥢 Ingredients :

For the topping:

✅ 6 canned pineapple rings (cut in half)

✅ 6 maraschino cherries (halved)

✅ 1/4 cup (60g) unsalted butter, melted

✅ 1/3 cup (65g) brown sugar

For the sugar cookie dough:

✅ 1/2 cup (113g) unsalted butter, softened

✅ 3/4 cup (150g) granulated sugar

✅ 1 large egg

✅ 1 tsp vanilla extract

✅ 1 1/2 cups (190g) all-purpose flour

✅ 1/2 tsp baking soda

✅ 1/4 tsp salt

👨‍🍳 Instructions :

1. Preheat oven to 350°F (175°C). Grease a 12-cup muffin tin well or line with non-stick spray.
2. Prepare the topping:
   • In each muffin cup, add about 1 tsp of melted butter and 1 tsp of brown sugar.
   • Place a pineapple half and half a cherry in each cup, pressing gently.
3. Make the cookie dough:
   • Beat the softened butter and granulated sugar in a large bowl until the mixture becomes light and fluffy.
   • Beat in the egg and vanilla extract.
   • In a separate bowl, whisk flour, baking soda, and salt.
   • Slowly incorporate the dry ingredients into the wet mixture, stirring until a soft dough comes together.
4. Assemble the cookies:
   • Scoop about 2 tablespoons of dough and gently flatten into a disc.
   • Place each dough disc over the pineapple-cherry topping in the muffin tin and press lightly.
5. Bake for 15–18 minutes, until the edges are golden.
6. Cool for 5 minutes, then carefully invert the cookies onto a wire rack or tray. Let cool completely.

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💡 TIPS :

• Use parchment strips in muffin cups for easier removal.
• Pat the pineapple slices dry to avoid soggy bottoms.
• Chill the dough for 15 minutes if it’s too sticky.
• For a caramelized effect, broil for 1–2 minutes at the end (watch closely!).

📊Nutrition Information (per cookie, approx):

Note: Values are estimates and can vary depending on ingredient brands.

❓ Pineapple Upside Sugar Cookies (FAQ ):

1. Can I use fresh pineapple instead of canned?
   Yes! Just make sure to slice it thinly and remove any tough core pieces. Make sure to blot it dry before using to remove any excess moisture.
2. Do I need to grease the muffin tin if I’m using non-stick?
   Yes, still grease it well or use a baking spray to ensure easy release since the caramelized sugar can stick.
3. Can I make the dough ahead of time?
   Definitely. You can prepare the sugar cookie dough up to 2 days in advance and keep it refrigerated in an airtight container.
4. Can I freeze these Pineapple Upside Sugar Cookies?
   Yes. Once baked and cooled, freeze in a single layer, then transfer to a container. Thaw at room temperature before serving.
5. Can I use store-bought sugar cookie dough?
   Yes, for a shortcut! It won’t be as rich or buttery as homemade, but it works well in a pinch.
6. Why did my Pineapple Upside Sugar Cookies stick to the muffin tin?
   This is usually due to not greasing enough or the sugar hardening as it cools. Let them sit for 5 minutes before inverting.
7. Can I bake these Pineapple Upside Sugar Cookies on a regular cookie sheet instead??
   No, the topping will run off. You need a muffin tin or ramekins to hold the caramel, pineapple, and cherry in place.
8. Are these Pineapple Upside Sugar Cookies overly sweet?
   They are sweet, like classic pineapple upside-down cake. You can reduce the brown sugar topping slightly if desired.
9. Can I add coconut or nuts to the Pineapple Upside Sugar Cookies?
   Absolutely! Shredded coconut or chopped pecans sprinkled into the topping or dough add great flavor and texture.
10. How long do this Pineapple Upside Sugar Cookies stay fresh?
    Store these Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to 3 days or refrigerate for up to 5 days.