Rolo Stuffed Cookies
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These Rolo stuffed chocolate cookies are going to be a new family favorite. Delicious, soft, and chewy chocolate cookies with an ooey gooey caramel center.
For more of my favorite thick and chewy cookie recipes give my kitchen sink cookies or cookie monster cookies a try.

What’s not to love about Rolo candies? You get the delicious chocolaty coating and then the rich, creamy, chewy caramel center.
But what if you surrounded that delicious candy in a chocolate cookie? It’s a cookie that everyone who loves chocolate and caramel are going to go fall in love with.
The Rolo flattens and melts a bit during baking, leaving the center of the cookie filled with the Rolo’s delicious, gooey caramel. Mmmmm so good! Especially when served warm, fresh from the oven with the center still gooey.

Your family is going to go crazy for these homemade Rolo stuffed cookies. Enjoy them with milk, hot chocolate, or a nice cup of coffee. However you serve them, they are sure to be a big hit.
Looking for cookie exchange recipes? These bad boys are perfect! If you want, you can make them a little bit more Christmasy by adding some green and red sprinkles on top.
These chocolate Rolo cookies would also make an amazing item for a bake sale because who can pass up caramel goodness?! No one. That’s right!
Looking for more stuffed cookie recipes? Try these homemade oatmeal cream pies, soft and chewy snickerdoodles or easy peppermint patty stuffed cookies. Both are incredible!

Rolo Stuffed Chocolate Cookies
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
- Preheat oven to 375℉ degrees. Line 2 cookie sheets with parchment paper.
- In a small bowl, whisk to combine flour, cocoa powder, and baking soda. Set aside.
- 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.
- Chill cookie dough in the refrigerator for 15 minutes.
- 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.
- 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

Did You Make This Recipe?
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Oh my. These sound so good. I love Rolo’s but I haven’t had them in a while. I can’t wait to make these. Thank you for sharing
Those cookies sound so good! Love a surprise inside like that.
Wow, this looks scrumptious. Im excited about trying it out this weekend. My family has been asking for something new. Thank you for sharing it.
I have the perfect occasion in mind for this dessert. Im so glad that I saw this recipe today. I know that it will be a hit!
these look so good,,my grandkids would gobble these right up
Thank you for sharing this! It looks absolutely incredible! I cant wait to try it.
Wow, that looks like a skillet cookie cake — perfect to celebrate any party with 🙂 🙂 My kids will LOVE this. Thanks for sharing this yummy recipe.
This looks so delicious and so fun. It’s a perfect weekend family dessert. Cast iron skillet desserts are super easy to make. I can’t wait to try your recipe and serve it to my family.
I have been looking for a great skillet cookie recipe for a long time now thats not chocolate. I finally found one that I cant wait to try here and its so pretty thanks for sharing!
Aww, a frosted cookie!! So cute. Love the pretty pink. I would so be able to have the whole skillet all by myself. I am a huge cookie monster. Saving this for later.