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Rolo Sugar Cookie Cups

Okay, friends, let me tell you about something that’s become a HUGE favorite around here: Rolo Sugar Cookie Cups. Picture this: soft, chewy sugar cookies transformed into little cups, each cradling a melty, gooey Rolo candy. It’s like a miniature caramel-chocolate explosion in every bite! It reminds me of a cross between classic sugar cookies and those thumbprint cookies we all love, but with a super-fun, candy twist that makes them incredibly irresistible. Honestly, I think I might even prefer these to plain sugar cookies now – shhh, don’t tell grandma!

Rolo Sugar Cookie Cups final dish beautifully presented and ready to serve

What is Rolo Sugar Cookie Cups?

So, what exactly *are* Rolo Sugar Cookie Cups? Well, think of it as a deconstructed, individual-sized sugar cookie topped with a delightful surprise. We’re talking about taking the classic sugar cookie – that buttery, slightly sweet treat we all know and love – and giving it a major upgrade. Instead of a flat cookie, we gently press the dough into mini muffin tins to create cute little cups. Then, before baking, each cup gets a Rolo candy nestled inside. As they bake, the cookie forms around the Rolo, and the caramel inside gets all melty and gooey. It’s essentially a bite-sized piece of heaven, perfect for parties, potlucks, or just a little treat for yourself. The name pretty much says it all – it’s sugar cookie dough shaped into cups with a Rolo candy inside!

Why you will love this recipe?

Oh, where do I even begin? There are SO many reasons to adore these Rolo Sugar Cookie Cups. First and foremost, the flavor is absolutely incredible. You’ve got the sweet, buttery richness of the sugar cookie perfectly balanced by the caramel and chocolate from the Rolo. It’s a match made in dessert heaven! Then there’s the simplicity – seriously, this recipe is a breeze. It’s so easy, even my eight-year-old can help (and she loves to!). What I love most about this is that it feels fancy and special, but it’s actually incredibly budget-friendly. The ingredients are all pantry staples, so you probably already have most of what you need on hand. Think of them like miniature sugar cookie pies, but way easier to make. And did I mention versatility? You can easily customize these with different sprinkles, frostings, or even different kinds of candies! If you’re a fan of chocolate and caramel, you’ll absolutely love these Rolo Sugar Cookie Cups. They are the perfect combination of flavors and textures. They are also perfect with a glass of milk or a cup of coffee. These are way better than any store-bought candy or cookies that I have ever tasted!

How do you make Rolo Sugar Cookie Cups?

Quick Overview

Making these Rolo Sugar Cookie Cups is easier than you might think! Basically, you’ll whip up a batch of simple sugar Cookie Dough, press it into mini muffin tins, pop a Rolo in each cup, and bake until golden brown. The magic happens in the oven as the Rolo melts into a pool of gooey caramel and the cookie turns perfectly soft and chewy. It is simple, and even a beginner baker can easily make this recipe!

Ingredients

For the Sugar Cookie Dough:
* 1/2 cup (1 stick) unsalted butter, softened to room temperature. Make sure the butter is actually soft, not melted! What makes a cookie’s texture different?
* 1/2 cup granulated sugar. Regular white sugar is perfect for this recipe.
* 1/4 cup packed light brown sugar. This adds a touch of molasses flavor and keeps the cookies soft.
* 1 large egg. Use a room temperature egg for better incorporation.
* 1 teaspoon vanilla extract. Don’t skimp on the vanilla! It enhances all the other flavors.
* 1 1/2 cups all-purpose flour. Spoon and level the flour to avoid using too much.
* 1/2 teaspoon baking soda. This helps the cookies rise and become tender.
* 1/4 teaspoon salt. Salt balances the sweetness and enhances other flavors.

For the Rolo Filling:
* 24 Rolo candies, unwrapped. You’ll need one for each cookie cup. I always buy an extra bag just in case!

Rolo Sugar Cookie Cups ingredients organized and measured on kitchen counter

How do I learn step

Step 1: Preheat & Prep Pan

Preheat your oven to 350°F (175°C). Lightly grease a 24-cup muffin tin with cooking spray. Trust me, you don’t want these sticking! I also sometimes dust the pan with a little flour for extra insurance.

Step 2: Cream Butter and Sugars

In a large bowl, cream together the softened butter, granulated sugar, and Brown Sugar until light. Set aside. This usually takes about 3-5 minutes with an electric mixer. The mixture should be pale and almost doubled in volume.

Step 3: Add Egg and Vanilla

Beat the egg and vanilla extract until well combined. Make sure to scrape down the sides of the bowl to ensure everything is evenly mixed.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the flour, baking soda, and salt. Set aside. This ensures that the baking soda and salt are evenly distributed throughout the flour.

Step 5: Gradually Add dry ingredients to wet ingredients.

Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Do not overmix cookies, as this can result in hard cookies.

Step 6: Shape Dough into Balls

Roll dough into 1-inch balls (about 1 tablespoon each). If the dough is too sticky, chill it in the refrigerator for 15-20 minutes.

Step 7: Press Dough into Muffin Tins

How do I make a mini muffin cup? Gently press each ball of dough into the bottom and up the sides of the muffin cups. Small cup shape.

Step 8: Add Rolos

Place one unwrapped Rolo candy in the center of each cookie cup.

Step 9: Bake

Bake for 8-10 minutes, or until the edges of the cookies are lightly golden brown. Keep a close eye on them, as they can burn easily.

Step 10: Cool and Enjoy

Let the cookies cool in the muffin tin for a few minutes before carefully transferring them to the pan. How do you cool a wire rack? If you try to remove them too soon, the Rolos might be too melty and the cookies could fall apart.

What should I serve it with?

These Rolo Sugar Cookie Cups are fantastic on their own, but they’re even better with the right accompaniments! For a casual afternoon treat, serve them with a cold glass of milk or a cup of hot cocoa. My kids love dunking them in milk! If you’re serving them at a party, arrange them on a pretty platter with a variety of other desserts, like brownies, cupcakes, or fruit skewers. They also pair perfectly with coffee or tea. For a more elegant presentation, drizzle them with melted chocolate or sprinkle them with chopped nuts. During the holidays, I like to add a dollop of whipped cream and a sprinkle of crushed peppermint candies. Honestly, the possibilities are endless! They are the perfect complement to a cup of black coffee!

How do you make Rolo Sugar Cookie Cups?

Want to make sure your Rolo Sugar Cookie Cups turn out perfectly every time? Here are a few of my top tips: First, make sure your butter is softened but not melted. Melted butter will result in flat, greasy cookies. If your dough is too sticky to handle, chill it in the refrigerator for 15-20 minutes before rolling into balls. Don’t overbake the cookies! They should be lightly golden brown around the edges but still soft in the center. Overbaking will result in dry, crumbly cookies. Let the cookies cool in the muffin tin for a few minutes before transferring them to a wire rack. This will prevent them from breaking apart. If you want to add a little extra flair, try sprinkling the cookies with coarse sea salt before baking. The salt enhances the sweetness and creates a delicious contrast of flavors. I also sometimes add a pinch of cinnamon to the dough for a warm, cozy flavor. Another great tip is to gently press the Rolo candy into the cookie dough, so it’s slightly submerged. This helps prevent it from melting too much and overflowing. And if you’re feeling adventurous, try using different kinds of candies instead of Rolos! Peanut butter cups, caramel squares, or even chocolate-covered pretzels would all be delicious. I have tried adding some peanut butter chips once, and it was delicious! You can also try adding some salt flakes to the cookies. This enhances the sweetness of the cookies. These little touches make all the difference!

What are some Storing and Reheating Tips?

These Rolo Sugar Cookie Cups are best enjoyed fresh, but they can also be stored for later. To store them at room temperature, place them in an airtight container and they’ll stay fresh for up to 3 days. If you want to store them for longer, you can refrigerate them in an airtight container for up to a week. Just be sure to let them come to room temperature before serving. For long-term storage, you can freeze them in a freezer-safe container for up to 2 months. When freezing, I like to wrap each cookie individually in plastic wrap before placing them in the container. This helps prevent freezer burn. To thaw, simply place the cookies in the refrigerator overnight or at room temperature for a few hours. I don’t recommend reheating these cookies, as the Rolos can become too melty. But if you really want to, you can microwave them for a few seconds until slightly warmed.

What are the most frequently asked questions on

How do I make this gluten free?
Can you substitute all-purpose flour with a gluten-free baking flour? I’ve had good results with Bob’s Red Mill Gluten Free 1-to-1 Baking Flour. Just be sure to add a pinch of xanthan gum to help with texture. What are some of the best cookies you’ve ever had?
Do I need to chill dough?
Can you chill the dough? It’s a warm day. Chilling for 15-20 minutes will firm up the butter and prevent the cookies from spreading too much.
Can I use different candies instead of Rolos?
Absolutely! Peanut butter cups, caramel squares, or even chocolate-covered pretzels would all be delicious substitutes. Just make sure the candies are small enough to fit inside the cookie cups.
How can I prevent the Rolos from melting too much?
Gently press the Rolos into the cookie dough, so they’re slightly submerged. This will help prevent them from melting too much and overflowing. Also, be sure not to overbake the cookies.
Can I add a glaze to these cookies?
Of course! A simple powdered sugar glaze would be a delicious addition. Just whisk together powdered sugar with a little milk or lemon juice until you reach your desired consistency. Drizzle the glaze over the cooled cookies.

Final Thoughts

Rolo Sugar Cookie Cups slice on plate showing perfect texture and swirl pattern

These Rolo Sugar Cookie Cups are seriously one of my favorite treats to make. They’re so easy, so delicious, and always a crowd-pleaser. Whether you’re baking for a party, a potluck, or just a cozy night in, these little gems are sure to bring a smile to everyone’s face. The combination of the soft sugar cookie and the gooey, melty Rolo is simply irresistible. If you enjoy this, maybe you would also enjoy my peanut butter cookie cups! I hope you give this recipe a try – I know you’ll love it! Happy baking!

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Rolo Sugar Cookie Cups

Rolo Sugar Cookie Cups

These Rolo Sugar Cookie Cups are a delicious combination of soft sugar cookies and gooey caramel chocolates, perfect for any occasion!
Prep : 10 Total : 25 minutes

Ingredients
  

Main Ingredients

  • 2.5 cups all-purpose flour sifted
  • 1 cup unsalted butter softened
  • 1.5 cups granulated sugar
  • 2 large eggs at room temperature
  • 1 tsp vanilla extract
  • 1 tsp baking powder
  • 24 Rolo chocolates unwrapped

Instructions
 

Preparation Steps

  • Preheat the oven to 350°F (175°C). Grease a mini muffin tin.
  • In a large bowl, cream together the butter and sugar until light and fluffy. Add in eggs and vanilla, beating well.
  • Gradually add in flour and baking powder, mixing until combined.
  • Scoop dough into the prepared muffin tin, filling each about 3/4 full.
  • Bake for 8-10 minutes or until edges are golden. Remove from oven and immediately press a Rolo into the center of each cookie cup.
  • Allow to cool in the pan for 10 minutes before transferring to a wire rack to cool completely.

Notes

These cookie cups are best enjoyed fresh, but they can be stored in an airtight container for up to 3 days.
Everydaycoockingtips

I’m Lina, a Certified Nutrition Coach, wellness advocate, and the heart behind EveryDayCookingTips. I’m passionate about helping you thrive—physically and mentally—through practical advice, inspiring articles, and wholesome, easy-to-make recipes. Pull up a seat—there’s always a place for you at this table!

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as seen on:

Everydarycookingtips
Everydarycookingtips
Everydarycookingtips
Everydarycookingtips
Everydarycookingtips
Easy Healthy Recipes

as seen on:

Everydarycookingtips
Everydarycookingtips
Everydarycookingtips
Everydarycookingtips
Everydarycookingtips
Easy Healthy Recipes

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