Preheat oven to 375°F and line baking sheet with parchment paper.
Combine butter, sugar, and brown sugar and cream together.
Add eggs and vanilla then beat until light and fluffy, about 2 minutes.
Combine baking soda, salt, and flour in a small bowl. Add mixture to wet ingredients and mix well.
Fold in chocolate chips.
Scoop out a ball of cookie dough using a medium scoop and make a balls of dough. Press a Rolo into the center of each ball, making sure to cover the Rolo completely with dough before placing on baking sheet.
Bake for 9 - 11 minutes. Let cool on baking sheet for 10 minutes before transferring to baking rack to cool completely.
Make sure to cover the Rolo completely in the middle of the cookie. If any of it is left uncovered, you’ll end up with caramel ooozing out on your baking sheet.Buy unwrapped Rolos to save you time having to unwrap all 36 of those little candies.Store leftover cookies in an airtight container and enjoy within five days.Make mini Rolo cookies by using a small cookie scoop to portion out your dough for the balls and filling the cookies with a miniature Rolo candy.