Rolo Cookies — soft, chocolate cookies with a gooey caramel center that are impossible to resist.
If you love chocolate, these cookies are for you. For other chocolate-forward treats, try Chocolate Truffle Cookies or Oreo Mint Chocolate Chip Cookies.
I always watch for after-holiday candy sales and stock up on baking supplies like Reese’s, M&Ms, and Rolos. They’re perfect for stuffing into cookies, and buying on sale means I can experiment more in the kitchen.
I hide my candy stash so family members don’t polish it off before I can bake with it—sometimes I even hide it from myself to avoid temptation.
A Perfect Cookie for Chocolate and Caramel Fans
These chocolate cookies are filled with Rolos so each bite reveals an ooey-gooey caramel center. They look simple from the outside but are decadently indulgent inside. Sprinkling sugar on top is optional but adds a pretty sparkle—dip just the tops of the dough balls in sugar or roll the entire ball if you prefer a sweeter crust.
If you enjoy chocolate paired with caramel, these Rolo-stuffed cookies are a must-try.
How to Make Chocolate Rolo Cookies
(Scroll to the recipe card at the bottom for the full recipe.)
Ingredients
- 1 cup softened butter (salted is fine)
- 1 cup granulated sugar
- 1 cup brown sugar (light or dark)
- 2 large eggs
- 2 tsp vanilla extract
- 2 ¾ cups all-purpose flour
- ½ cup unsweetened cocoa powder
- 1 tsp baking soda
- ½ tsp baking powder
- ½ tsp salt
- About 42 unwrapped Rolo candies
- ¼ cup granulated sugar for rolling
Tips and Instructions
Prep: Preheat the oven to 350°F. Line baking sheets with parchment or silicone mats or spray lightly with nonstick spray. Pour ¼ cup sugar into a small bowl and unwrap the Rolos.
Cream: In a large bowl, beat the softened butter with both sugars until creamy. The butter should be soft but not melted to ensure a smooth texture.
Wet ingredients: Beat in the eggs one at a time, then stir in the vanilla.
Dry ingredients: Whisk together the flour, cocoa, baking soda, baking powder, and salt. Stir the dry ingredients into the wet ingredients by hand with a wooden spoon or spatula to avoid overmixing; this helps keep the cookies tender.
Form cookies: Take about one tablespoon of dough and wrap it completely around a Rolo, sealing the edges well so the caramel doesn’t leak during baking. Dip the top of each cookie in the reserved sugar and place sugar-side up on the prepared baking sheet.
Bake: Bake at 350°F for about 9 minutes, or until the cookies are set around the edges but still soft in the center.
Cool: Let the cookies rest on the baking sheet for a couple of minutes before transferring them to a cooling rack to finish cooling.
Serve: These cookies are especially delicious warm, when the caramel is soft and oozing. Enjoy with a glass of cold milk.
Storage
Store cooled cookies in an airtight container at room temperature for 4–5 days. They also freeze well: place cooled cookies in heavy-duty freezer bags and freeze for up to 3–4 months. To serve from frozen, thaw at room temperature or microwave 20–30 seconds—use caution, as the caramel can become very hot.
More Made-from-Scratch Cookies
- Brookies
- Brown Sugar Shortbread
- Chocolate Reese’s Peanut Butter Cookies
- Chocolate Cookie Cups (with peanut butter mousse)
- Italian Cookies
- Cherry Shortbread Cookies
- Nutella Peanut Butter Cookies
- Peanut Butter Cup Cookies
- Lemon Sugar Cookies
- Butter Cookies with Lemon Cream Cheese Frosting
- Double Chocolate Kiss Cookies
- Gingersnaps (white chocolate dipped)
Rolo Cookies (Caramel Filled Chocolate Cookies)
Rolo Cookies
Kara
20 mins
9 mins
29 mins
Dessert: Cookies
American
42 cookies
149 kcal
Equipment
- Hand mixer
- Silicone baking mat or parchment-lined baking sheets
Ingredients
- 1 cup soft butter
- 1 cup sugar
- 1 cup brown sugar
- 2 eggs
- 2 tsp vanilla
- 2 ¾ cups flour
- ½ cup unsweetened cocoa powder
- 1 tsp baking soda
- ½ tsp baking powder
- ½ tsp salt
- 42 Rolos, unwrapped
- ¼ cup sugar for tops
Instructions
- Preheat oven to 350°F.
- Cream butter and sugars. Beat in eggs and vanilla.
- Sift or whisk dry ingredients and stir into the wet mixture until just combined.
- Wrap about 1 tablespoon of dough around each Rolo, sealing well. Dip tops in sugar and place sugar-side up on prepared baking sheets.
- Bake 9 minutes. Cool 2 minutes on the pan, then transfer to a rack to cool completely.
Nutrition
Let us know how it was!
See more cookie recipes in my COOKIE RECIPES collection.