Rolo Cookies are soft and chewy chocolate cookie that are stuffed with a Rolo Candy. When they bake the Rolo melts making a fudgy chocolate center with melted caramel.
Preheat the oven to 375°. Line one or two cookie sheets with parchment paper or reusable silpats. Pour ¼ cup sugar in a small bowl - set aside.Unwrap about 30 Rolo candies.
Sift together the flour, unsweetened cocoa powder, salt, and baking soda.Pro Tip: sift onto a large piece of parchment paper. Then pick it up two sides, like a tube, so you can easily slide the ingredients into the mixing bowl.
2 ½ cups all purpose flour, ¾ cup unsweetened cocoa powder, 1 teaspoon baking soda, ¼ teaspoon salt
Chocolate Cookie Dough
In a stand mixer with the paddle attachment (or a bowl with a hand mixer) cream together the 1 cup softened butter, 1 cup brown sugar, 1 cup white sugar, until it is creamy and fluffy, about 4 minutes.
Add the 2 teaspoon vanilla and 2 eggs to the butter mixture, mix together until it is well combined, about 1 minute.
Add the sifted flour/cocoa mixture to the butter mixture, in batches. Only beat until it is combined.
Using a tablespoon scoop out a generous tablespoon of cookie dough and place it in the palm of your hand. Press one Rolo into the center of the dough. Form the dough around the Rolo, covering it completely.
Roll the cookie in the sugar, covering all sides. Place on the cookie sheet.
Baking
Bake the cookies 9-12 minutes. Time will depend on your cookie sheet:Dark colored cookie sheets - 9-10 minutesLight colored cookie sheets - 11-12 minutes.
Pro Tip: if cooking in batches, place the cookie dough in the fridge while each batch bakes.
If you like a sweet and salty cookie, right when the cookies come out of the oven you can sprinkle a little flaky sea salt over top!
Let the cookies cool for a few minutes and then enjoy!
Freezing
See Notes.
Notes
STORING COOKIES: You can store your leftover Rolo cookies at room temp in an airtight container for up to 5 days. They will be softest the first couple days!FREEZING ROLO COOKIES: You can freeze your Rolo Cookies or cookie dough!
Baked Cookies - cool completely and then place in an airtight & freezer safe container. Freeze for up to 3 months.
Cookie Dough - Prepare the cookies completely but do not roll in the sugar. Place in an airtight & freezer safe container and keep frozen for up to 3 months. When you are ready to bake them, bake from frozen- roll in sugar and bake for 11-12 minutes. May need a minute or two longer since they were frozen.