Irresistible Rolo Stuffed Chocolate Cookies: Your New Favorite Gooey Treat
Prepare to fall in love with these Rolo stuffed chocolate cookies! Imagine a perfectly baked, soft, and unbelievably chewy chocolate cookie, giving way to a warm, luscious, and ooey-gooey caramel center. This isn’t just any cookie; it’s a delightful explosion of chocolate and caramel that promises to become an instant family favorite in your home. Each bite delivers a harmonious blend of rich cocoa and sweet, melted Rolo candy, creating a truly unforgettable dessert experience.
If you’re a fan of thick, satisfyingly chewy cookies with exciting fillings, then you’re in for a real treat. For those who enjoy exploring more unique cookie creations, be sure to give my kitchen sink cookies or cookie monster cookies a try. They offer similar levels of delightful texture and flavor combinations, but these Rolo cookies truly stand out with their surprise caramel core.

The Enduring Appeal of Rolo Candies
What’s not to adore about Rolo candies? Each little piece is a miniature marvel, perfectly crafted to deliver a dual sensation. You first encounter the smooth, decadent milk chocolate coating, a classic flavor that prepares your palate for what’s inside. Then, as you bite down, you discover the rich, creamy, and wonderfully chewy caramel center. This iconic combination of chocolate and caramel has captivated taste buds for generations, making Rolo a beloved treat in its own right.
But imagine taking that already perfect candy and elevating it to an entirely new level. What if you enveloped that beloved Rolo in a rich, homemade chocolate cookie? That’s precisely what we’ve done here, creating a dessert that marries two beloved treats into one spectacular experience. It’s a cookie designed for anyone who cherishes the classic pairing of chocolate and caramel, promising a dessert that will undoubtedly become a personal favorite.
Why These Rolo Stuffed Cookies Are a Must-Try
The magic truly happens in the oven. As these cookies bake to golden-brown perfection, the Rolo candy nestled within the dough transforms. The chocolate coating of the Rolo melts and blends seamlessly with the rich chocolate cookie dough, while the caramel center softens and flattens, creating an incredibly delicious, gooey pocket of caramel. This results in a cookie with a molten, flowy caramel core that is simply irresistible. The aroma alone as they bake is enough to make your mouth water!
The experience is particularly sublime when these chocolate caramel cookies are served warm, fresh from the oven. The ooey-gooey caramel remains wonderfully fluid, stretching delightfully with each bite. It’s a sensory pleasure that combines the comforting warmth of a freshly baked cookie with the luxurious sweetness of melted caramel. This unique texture and flavor profile are what set these Rolo stuffed cookies apart, making them a truly special homemade treat.

Perfect for Any Occasion
Your family will undoubtedly go absolutely wild for these homemade Rolo stuffed cookies. They are the kind of treat that brings smiles and prompts requests for “just one more.” Whether it’s a quiet evening at home or a bustling gathering, these cookies are a guaranteed crowd-pleaser. Pair them with a tall glass of cold milk for a classic comfort experience, a mug of rich hot chocolate for an extra layer of indulgence, or a nice, hot cup of coffee to balance their sweetness. However you choose to serve them, they are destined to be a big hit and leave everyone craving more.
Beyond daily enjoyment, these cookies are incredibly versatile for various events. Are you looking for standout cookie exchange recipes during the holiday season? These delectable treats are absolutely perfect! To give them an extra festive touch, simply add some vibrant green and red sprinkles on top before baking. Their unique surprise center will make them the talk of any holiday party. Moreover, these chocolate Rolo cookies would make an amazing item for a bake sale. Who, after all, can resist the allure of gooey caramel enveloped in rich chocolate? No one, that’s who! They’re sure to sell out fast and raise plenty of funds for a good cause.
Craving More Stuffed Cookie Goodness?
If you’ve discovered a love for cookies with delightful surprises inside, you’re in luck! The world of stuffed cookies is vast and incredibly delicious. After enjoying these Rolo-filled delights, why not explore other recipes that offer a similar joy of discovery? Try these homemade oatmeal cream pies for a nostalgic twist, or delve into the soft and chewy perfection of our jumbo soft snickerdoodles – while not “stuffed” in the traditional sense, their pillowy texture and cinnamon-sugar coating are equally addictive. For another unique filled experience, our easy peppermint patty stuffed cookies are absolutely incredible, offering a refreshing minty burst within a rich chocolate cookie. Each of these recipes promises a unique and satisfying baking adventure!

Rolo Stuffed Chocolate Cookies
Author: Jaclyn
Ingredients
- 2 ½ cups all-purpose flour
- ¾ cup unsweetened cocoa powder
- 1 teaspoon baking soda
- 1 cup granulated sugar
- 1 cup light brown sugar packed
- 1 cup unsalted butter room temperature
- 2 teaspoons vanilla extract
- 2 large large eggs room temperature
- 48 Rolo candies unwrapped
Instructions
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Preheat oven to 375℉ degrees. Line 2 cookie sheets with parchment paper.
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In a small bowl, whisk to combine flour, cocoa powder, and baking soda. Set aside.
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Using an electric mixer, beat brown sugar, white sugar, and butter in a large bowl until smooth and creamy. Mix in vanilla and eggs. With the mixer on low slowly add flour mixture one Tablespoon at a time, mixing until just combined.
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Chill cookie dough in the refrigerator for 15 minutes.
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Scoop 1 Tablespoon of dough at a time and wrap it around a Rolo candy to form a ball. Place dough balls on the lined cookie sheet about 2 inches apart.
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Bake at 375℉ for 7-10 minutes or until the cookies are set and just start to crack. Allow the cookies to cool on the cookie sheet for 4-5 minutes, then move to a wire rack.
Notes
Nutrition
Tips for Baking the Perfect Rolo Stuffed Chocolate Cookies
Achieving bakery-quality cookies at home is easier than you think, especially with a few handy tips. These Rolo stuffed chocolate cookies, while straightforward, benefit from some expert advice to ensure they turn out perfectly gooey and chewy every single time:
- Room Temperature Ingredients: Ensure your butter and eggs are at room temperature. This is crucial for creating a smooth, creamy dough. Room temperature butter creams better with sugar, incorporating more air and resulting in a lighter, more tender cookie. Eggs at room temperature emulsify more easily into the mixture, preventing a curdled appearance and contributing to a uniform texture.
- Don’t Overmix: Once you add the dry ingredients to the wet, mix only until just combined. Overmixing develops the gluten in the flour, which can lead to tough, dry cookies instead of the soft, chewy texture we’re aiming for. A few streaks of flour are fine; they’ll disappear during the next mixing step or during baking.
- Chilling the Dough is Key: The 15-minute chill time is not optional! Chilling the dough solidifies the butter, which helps prevent the cookies from spreading too much in the oven. It also allows the flavors to meld and the flour to fully hydrate, resulting in a richer flavor and better texture. This brief chill makes the dough easier to handle when wrapping around the Rolo candies.
- Unwrap Rolos in Advance: Save yourself some sticky fingers and unwrap all 48 Rolo candies before you start assembling the cookies. This makes the process much quicker and more enjoyable.
- Completely Encase the Rolo: When forming the dough balls around the Rolo, make sure the candy is completely covered by the dough. Any exposed Rolo will cause the caramel to seep out and burn on the cookie sheet, which is a waste of that delicious gooey center!
- Parchment Paper is Your Friend: Always line your baking sheets with parchment paper. It prevents sticking, ensures even baking, and makes cleanup a breeze. Plus, it helps the cookies slide off easily once cooled.
- Don’t Overbake: These cookies are best when slightly underbaked. They should be set around the edges and just starting to crack, but the centers might still look a little soft. They will continue to cook slightly as they cool on the hot baking sheet. This ensures that signature soft and chewy texture with a truly gooey caramel center.
- Cooling Time: Allowing the cookies to cool on the baking sheet for 4-5 minutes is important. This helps them firm up slightly before you attempt to transfer them to a wire rack, preventing them from falling apart.
Delicious Variations to Try
While these Rolo stuffed chocolate cookies are perfect as they are, there’s always room for creativity in the kitchen! Here are a few ideas to customize your next batch and keep things exciting:
- Different Candies: Not a Rolo fan or looking for a different flavor profile? Try stuffing your cookies with other small, melty candies. Miniature Reese’s Peanut Butter Cups, caramels, or even a square of your favorite chocolate bar (milk, dark, or white) can create equally delightful surprises.
- Add a Sprinkle of Salt: A pinch of flaky sea salt sprinkled on top of each cookie before baking can really enhance the chocolate and caramel flavors, offering a sophisticated sweet and salty contrast.
- Extra Chocolate Chips: For the ultimate chocolate lover, fold in half a cup of mini chocolate chips into the cookie dough before chilling. This adds even more chocolatey goodness and texture.
- Nutty Additions: If you enjoy nuts, try mixing in half a cup of chopped pecans or walnuts into the cookie dough. They add a lovely crunch and earthy flavor that pairs well with chocolate and caramel.
- Holiday Flair: As mentioned, adding green and red sprinkles is perfect for Christmas. For other holidays, switch up the sprinkle colors! Orange and black for Halloween, pastels for Easter, or even patriotic red, white, and blue for summer celebrations.
Frequently Asked Questions (FAQs)
Here are some common questions about making and enjoying these Rolo Stuffed Chocolate Cookies:
- Can I make the dough ahead of time? Yes! You can prepare the dough and chill it in the refrigerator for up to 2-3 days. This is perfect for meal prepping or when you want fresh cookies on demand. Just allow the dough to come closer to room temperature for easier handling when it’s time to stuff the Rolos.
- What if I don’t have parchment paper? While parchment paper is highly recommended, you can use a silicone baking mat or lightly grease your cookie sheets. However, parchment paper offers the best non-stick surface and easiest cleanup.
- How do I store leftover cookies? Store these cookies in an airtight container at room temperature for up to 4 days. If you want to enjoy that signature gooey center, simply pop a cookie in the microwave for 10-15 seconds before eating.
- Can I freeze these cookies? Yes, these cookies freeze beautifully! You can freeze the baked cookies in an airtight container for up to 3 months. Thaw at room temperature or warm slightly in the microwave. Alternatively, you can freeze the raw, Rolo-stuffed cookie dough balls. Place them on a baking sheet to freeze solid, then transfer to a freezer-safe bag. When ready to bake, place frozen dough balls on a parchment-lined sheet and bake for an extra 2-4 minutes, or until done.
- My Rolo melted out of the cookie, what went wrong? This usually happens if the Rolo wasn’t completely encased in dough, or if the dough wasn’t sufficiently chilled, causing it to spread too quickly. Ensure the Rolo is fully covered and try chilling the dough for a bit longer if you experience this issue.

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