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Rolo Stuffed Chocolate Chip Cookies

If there’s one food holiday we can get behind, it’s National Chocolate Chip Cookie Day! We’ve taken our favorite tried-and-true Joy of Baking chocolate chip cookie recipe and one-upped it by stuffing them with Rolos. Yup, we went there. 😍 Oh my goodness, these are dangerously good! Fresh out of the oven, they’re crisp on the outside and oozing with chocolate chips and caramel on the inside. Once they’ve cooled off, the caramel solidifies and becomes chewy again and it would be a tough choice to say which incarnation we prefer… 🤔🤷🏻‍♀️


(makes about 32 regular chip cookies and about 20 Rolo stuffed cookies)

1 cup (225 grams) unsalted butter at room temperature

3/4 cup (150 grams) granulated white sugar

3/4 cup (160 grams) light brown sugar (firmly packed)

2 large eggs, at room temperature

1 1/2 teaspoons (6 grams) pure vanilla extract

2 1/4 cups (295 grams) all-purpose flour

1 teaspoon (4 grams) baking soda

1/2 teaspoon (2 grams) salt

1 1/2 cups (270 grams) semisweet or bittersweet chocolate chips

Ca. 20-25 Rolos, but can you ever have enough?


  1. In the bowl of your electric stand mixer, fitted with the paddle attachment (or with a hand mixer), beat the butter until smooth. Add the white and brown sugars, and vanilla extract, and beat until smooth and fluffy (about 1 - 2 minutes). Add the eggs, one at a time, beating until incorporated. Scrape down the sides and bottom of the bowl as needed.

  2. In a separate bowl, whisk the flour with the baking soda and salt. Add the dry ingredients, and chocolate chips, to the egg mixture and beat just until incorporated. Use a tablespoon or a small 1/8 inch ice cream scoop (if you’re using this it should be heaped!) and make one mound in to the palm of your hand. Press a Rolo into the middle. Top with another tablespoon of dough and roll gently between your palms to make a ball. Place on a baking sheet lined with parchment paper. Repeat until all dough is used up. Refrigerate for an hour. This will stop the cookies from spreading out too much.

  3. Preheat your oven to 375 F (190 C) and place the oven rack in the center of the oven. Line two baking sheets with parchment paper. When your dough has chilled enough, place the dough balls on the baking sheets. They need room to spread out, so we would suggest not crowding them, 6 dough balls per baking sheet is enough. You’ll probably have to bake them in batches, depending on how many baking sheets you have and how big your oven is. Bake for 10-12 minutes or until the edges are a light gold brown.

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