There’s a special thrill that comes from biting into a cookie and discovering a gooey surprise within. That’s exactly what you experience with these Rolo Stuffed Chocolate Cookies! I’ll never forget the first time I made this delightful treat; the soft chocolate exterior gives way to warm, melted caramel and chocolate that envelops your taste buds in a comforting embrace.
After a particularly hectic week filled with fast food meals that left me craving some homemade goodness, I decided it was time to whip up a batch of cookies that would satisfy my sweet tooth and wow my friends. These cookies are deceptively simple to make, and in just 30 minutes, you can transform a few pantry staples into a crowd-pleasing dessert that’s sure to impress.
Whether you’re looking to elevate your baking game or simply want a delicious reason to enjoy a cozy evening at home, these Rolo Stuffed Chocolate Cookies are the perfect answer. Grab your apron, and let’s get baking!

Why are Rolo Stuffed Chocolate Cookies essential?
Indulgence at its finest: Imagine biting into a cookie and finding a melty Rolo waiting inside — pure bliss!
Quick preparation: With just 30 minutes from start to finish, you can have fresh cookies ready to indulge.
Crowd-pleaser: Easy to share, these cookies make any gathering feel special and festive.
Unique twist: The combination of chocolate and caramel creates a delightful surprise in every bite.
Versatile treat: Perfect for birthdays, holidays, or simply a comforting dessert at home.
You won’t want to miss making these delicious delights that turn ordinary cookie time into a memorable experience!
Rolo Stuffed Chocolate Cookies Ingredients
• Discover the sweet magic within!
- 2 ½ cups all-purpose flour – essential for structure and texture
- ¾ cup unsweetened cocoa powder – for that rich chocolate flavor
- 1 teaspoon baking soda – helps the cookies rise and stay soft
- 1 cup granulated sugar – for sweetness and a slight crunch
- 1 cup light brown sugar (packed) – adds depth and moisture
- 1 cup unsalted butter (room temperature) – ensures a creamy dough
- 2 teaspoons vanilla extract – enhances the overall flavor
- 2 large eggs (room temperature) – binds the ingredients together
- 48 Rolo candies (unwrapped) – the star ingredient that brings gooey delight
Get ready to elevate your baking with these Rolo Stuffed Chocolate Cookies!
How to Make Rolo Stuffed Chocolate Cookies
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Preheat oven: Start by preheating your oven to 375°F (190°C). This ensures an evenly baked cookie that’s perfectly crisp on the outside and chewy inside.
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Mix dry ingredients: In a small bowl, whisk together the flour, cocoa powder, and baking soda. This step helps combine the flavors and aerate the mixture for a light texture.
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Cream sugars and butter: Using an electric mixer, beat together the granulated sugar, brown sugar, and softened butter in a large bowl until smooth and creamy. Add in the vanilla extract and eggs, mixing until well combined.
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Incorporate dry mix: With the mixer on low, gradually add the flour mixture one tablespoon at a time. Mix just until everything is combined; overmixing may lead to dense cookies.
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Chill the dough: Pop the cookie dough into the refrigerator for 15 minutes to firm up a bit. This will help the cookies maintain their shape while baking.
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Shape the cookies: Scoop about 1 tablespoon of dough and wrap it around each unwrapped Rolo candy, forming a ball. Place these dough balls on the lined cookie sheet, spacing them about 2 inches apart.
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Bake: Bake the cookies in the preheated oven for 7-10 minutes, or until the edges are set and cracks form on top. They should still feel soft to the touch but will firm up as they cool.
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Cool down: Allow the cookies to cool on the baking sheet for 4-5 minutes before transferring them to a wire rack. This resting time helps enhance the texture.
Optional: Drizzle with melted chocolate for an extra special touch.
Exact quantities are listed in the recipe card below.

What to Serve with Rolo Stuffed Chocolate Cookies?
Indulge in a delightful selection of pairings that enhance the decadence of your cookie experience!
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Cold Glass of Milk: The classic choice! Milk complements the gooeyness of the Rolo and balances the rich chocolate flavors effortlessly.
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Vanilla Ice Cream: This creamy addition takes your cookie to new heights, creating a divine sundae perfect for any dessert lover. A scoop atop a warm cookie is pure bliss!
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Fresh Berries: The tartness of strawberries or raspberries offers a refreshing contrast to the sweet cookie, brightening each bite and adding a pop of color.
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Chocolate Ganache: Drizzling warm chocolate ganache on top intensifies the chocolate flavor while adding a silky texture that chocolate enthusiasts adore.
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Coffee or Espresso: Pair your cookies with a hot cup of coffee for a delightful treat that awakens the senses and balances the sweetness beautifully.
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Caramel Sauce: For added decadence, drizzle warm caramel sauce over your cookies. Its buttery richness harmonizes perfectly with the melted Rolo inside.
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Nutty Brownies: Serve with a side of brownies for a chocolate lover’s dream platter! The nutty flavors provide an exciting texture and taste variety.
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Minty Tea: A comforting cup of peppermint tea can cleanse your palate, making the sweet finish of the cookies feel lighter and satisfying.
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Whipped Cream: Light and airy whipped cream on the side enhances your cookie experience, adding a delicate touch to each delightful bite.
Think of these wonderful options as invitations to create a memorable dessert spread that everyone will cherish!
Rolo Stuffed Chocolate Cookies Variations
Feel free to get creative and make this delightful recipe your own!
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Nutty Addition: Fold in ½ cup of chopped nuts for a delightful crunch that complements the gooeyness of the Rolo.
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Spicy Kick: Add a pinch of cayenne pepper to the dough for an unexpected heat that plays beautifully with the chocolate and caramel.
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Minty Fresh: Substitute vanilla extract with peppermint extract for a refreshing twist that brings the holiday spirit to your cookies.
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Dairy-Free: Use coconut oil instead of butter and almond or oat milk in place of regular milk to make these cookies dairy-free yet still delicious.
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Gourmet Drizzle: Melt white chocolate and drizzle it over the cooled cookies for a delightful contrast of flavors and a beautiful presentation.
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Stuffed Alternatives: Replace Rolo candies with caramel-filled chocolate or peanut butter cups for a fun surprise in every bite and a whole new flavor experience.
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Salted Caramel: Top each cookie with a sprinkle of sea salt before baking, enhancing the caramel’s flavor and satisfying that sweet-salty craving.
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Chocolate Chips: Fold in 1 cup of chocolate chips to double the chocolatey goodness. This creates a richer, even more indulgent cookie experience.
How to Store and Freeze Rolo Stuffed Chocolate Cookies
Room Temperature: Keep cookies in an airtight container at room temperature for up to 3 days to retain their soft texture.
Fridge: For longer freshness, store in the refrigerator for up to a week. Just be sure to wrap them tightly to prevent drying out.
Freezer: Freeze the cookies in a freezer-safe bag or container for up to 3 months. Layer parchment paper between cookies to avoid sticking.
Reheating: To enjoy warm cookies, simply reheat them in a microwave for about 10-15 seconds or in the oven at 350°F (175°C) for a few minutes.
Make Ahead Options
These Rolo Stuffed Chocolate Cookies are perfect for busy home cooks looking to save time while still enjoying a delightful homemade treat! You can prepare the cookie dough up to 24 hours in advance. Simply follow the recipe up to the chilling step, and then wrap the dough tightly in plastic wrap and refrigerate. This not only enhances the flavor but also helps maintain the cookie’s texture. When you’re ready to bake, scoop the dough and wrap it around the Rolo candies before baking as instructed. You’ll have fresh, gooey cookies on hand whenever you need them, making them just as delicious as if they were baked the same day!
Tips for the Best Rolo Stuffed Chocolate Cookies
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Use room temperature ingredients: Ensure your butter and eggs are at room temperature for a smoother mixing process; it helps create the perfect texture in your Rolo stuffed chocolate cookies.
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Don’t overmix: Combine the dry and wet ingredients just until incorporated. Overmixing can lead to tough cookies contrary to the soft, chewy texture we crave.
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Proper chilling time: Don’t skip the 15-minute chill time! This step firms up the dough, preventing the cookies from spreading too much while baking.
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Monitor baking time: Keep a close eye on the cookies as they bake. Pull them out as soon as the edges are set, even if they look slightly underbaked; they will continue to cook as they cool.
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Let them cool: Allow cookies to cool on the baking sheet for a few minutes before transferring them to a wire rack; this keeps them from breaking apart.
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Experiment with add-ins: Feel free to get creative by adding nuts or sprinkling sea salt on top for a delightful contrast to the sweetness of the Rolo stuffed chocolate cookies.

Rolo Stuffed Chocolate Cookies Recipe FAQs
How do I choose ripe and fresh ingredients for Rolo Stuffed Chocolate Cookies?
Absolutely! For the best results, make sure your butter is at room temperature, which ensures it creams well with the sugars. As for the eggs, use ones that are also at room temperature to help create a smooth batter. When selecting your Rolo candies, check for any that feel too soft or appear dusty on the surface, as those may not melt as beautifully in the cookies.
How should I store Rolo Stuffed Chocolate Cookies?
You can store your cookies at room temperature in an airtight container, where they’ll stay fresh for about 3 days. If you want them to last longer, pop them in the fridge for up to a week. Just make sure they’re wrapped tightly to prevent them from drying out!
Can I freeze Rolo Stuffed Chocolate Cookies?
Very! Freezing these cookies is a fantastic way to prolong their deliciousness. Place cooled cookies in a freezer-safe bag or container, making sure to layer parchment paper between them to avoid sticking. They’ll last for up to 3 months in the freezer. To thaw, simply let them sit at room temperature for several minutes or heat them in the microwave for 10-15 seconds for that fresh-from-the-oven feel.
What if my cookies spread too much while baking?
If you find your cookies are spreading excessively, don’t worry—it’s a common occurrence! This often happens if the dough hasn’t chilled long enough. Make sure to chill for the recommended 15 minutes before baking. Additionally, ensure that your butter is at the right temperature; too soft butter can lead to cookies that spread out too much. If they still spread, try adding a bit more flour next time!
Are Rolo Stuffed Chocolate Cookies safe for pets or those with allergies?
While these cookies are delicious for humans, they are not safe for pets, particularly because chocolate is toxic to dogs and cats. For allergic individuals, note that these cookies contain common allergens like gluten from flour, dairy from butter, and eggs. Always check ingredient labels and consult your doctor if you’re unsure.
Can I modify the recipe for special diets?
Definitely! If you’re looking for a gluten-free version, you can substitute the all-purpose flour with a gluten-free blend. For a dairy-free option, use coconut oil or dairy-free butter and substitute with a plant-based milk. However, please note that meal modifications can affect the texture and taste, but experimenting is part of the fun!

Indulgent Rolo Stuffed Chocolate Cookies You Can’t Resist
Ingredients
Equipment
Method
- Preheat your oven to 375°F (190°C).
- In a small bowl, whisk together the flour, cocoa powder, and baking soda.
- Using an electric mixer, beat together the granulated sugar, brown sugar, and softened butter until smooth and creamy. Add in the vanilla extract and eggs, mixing until well combined.
- With the mixer on low, gradually add the flour mixture one tablespoon at a time. Mix until everything is combined.
- Pop the cookie dough into the refrigerator for 15 minutes to firm up.
- Scoop about 1 tablespoon of dough and wrap it around each unwrapped Rolo candy, forming a ball. Place these dough balls on the lined cookie sheet, spacing them about 2 inches apart.
- Bake the cookies for 7-10 minutes, until the edges are set and cracks form on top.
- Allow the cookies to cool on the baking sheet for 4-5 minutes before transferring them to a wire rack.




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