Rolo Cookies

A sugar crusted chocolaty cookie wrapped around a sweet caramel Rolo candy.

Course Dessert

Cuisine American

Prep Time 5

Cook Time 10

Chilling Time 30

Total Time 15

Servings 3 dozen

In a large bowl, start by creaming your butter and sugars together until light and fluffy. Add the eggs and vanilla. Mix well.
In a medium bowl, combine flour, cocoa and baking soda with a whisk until well mixed. Add to the creamed mixture in 3 batches and beat until combined. You will end up with a stiff dough. I like to put my cookie dough in the fridge for 30 minutes to let it stiffen up a little bit because once you start rolling it into balls, the heat from your hand will make it sticky and harder to handle.
While the dough is chilling, unwrap the Rolos and preheat the oven to 275 degrees F. (And no, that's not a typo. It really is 275 degrees F.)
When the dough is chilled, use a spoon to scoop the dough and shape into tablespoon sized balls. To make a space for the Rolo, I use my thumb to make a divot in the ball, then form the dough around it. Pour 1/3 to 1/2 cup white sugar in a bowl or on a plate and roll the cookie in it before placing on the cookie sheet. I always use my silicone baking mat when I'm making cookies. It cleans up so well which is great, especially when you're dealing with caramel.
Place the cookies in the oven for 10-12 minutes or until slightly cracked. Remove from the oven and let cool for 3 minutes before trying to scoop them off the tray onto a wire rack to cool completely.