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.

Rolo stuffed chocolate cookies piled on wooded cutting board with one cookie sliced in half to show rolo inside.

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.

Chocolate cookie sliced in half to show caramel candy center.

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!

Recipe

5 from 15 votes

Rolo Stuffed Chocolate Cookies

Author: Jaclyn

Prep: 20

Cook: 10

Total: 30

These Rolo stuffed chocolate cookies are going to be a new family favorite. Delicious, soft, and chewy chocolate cookies with an ooey gooey Rolo center.

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

Although best served warm, these cookies can be stored in an airtight container at room temperature for up to 4 days.

Nutrition

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Ooey Gooey Rolo Stuffed Chocolate Cookies Pinterest image.

14 Comments

Cookies are one of my very favorite treats! And if I can make it in one skillet instead of making perfect little rounds on a cookie sheet – well, that’s even better. I like the nice thick wedge — it looks so yummy. Great idea.