These cookies bake in the pan and then you press a Rolo into each cookie once they come out of the oven. As they cool, the cookie sinks a little in the center, which makes that easy. The original recipe topped these cups with a whipped cream/mousse. I know that whipped cream isn’t necessarily as sturdy as frosting, so I opted to make a caramel-infused buttercream instead. I used some prepared (bourbon) caramel that I had on hand; you could certainly make plain buttercream if you wanted.
This recipe stated that it makes 24 cookies. I had thought about making one and a half or a double recipe, and I am glad that I didn’t. In the end I made 4 dozen cookie cups, which some dough left over. Mini muffin cups are a standard size and I certainly couldn’t have filled them any more, so I am not sure how you could only get 24 cookies. The frosting recipe is standard and does make more than you need for the batch of cookie cups. These are quite decadent, which chocolate chip cookie, paired with caramel, topped with frosting. I’m a fan of anything with caramel, so I was very happy with how these turned out.
Rolo Chocolate Chip Cookie Cups
3/4 cup butter, room temperature
1/2 cup sugar
1 cup packed brown sugar
1 teaspoon vanilla
2 cups flour
1 teaspoon baking soda
1/2 teaspoon salt
1 cup mini chocolate chips
¾ cup butter, room temperature
3 cups powdered sugar
1 teaspoon vanilla
¼ cup caramel sauce
3-4 tablespoons milk
Preheat oven to 350 degrees. Spray mini muffin pans with nonstick cooking spray.
In a large mixer bowl, mix the butter, sugar, and brown sugar on medium until smooth. Add the egg and vanilla and stir to combine. Add the flour, baking soda, and salt and mix on low until combined. Add the mini chocolate chips, stirring again on low to combine.
Scoop the dough into the muffin cups, filling about half full. Bake for 9-10 minutes, until lightly browned. Allow the cookies to cool for a couple of minutes before pressing a Rolo in the center of each cookie cup. Allow the cookies to cool completely before removing from the muffin pans.
Make the frosting: in a large mixer bowl beat the butter, powdered sugar, vanilla and caramel until smooth. Gradually add milk until the frosting is of the desired consistency. Pipe the frosting onto the cooled cookie cups. Sprinkle with additional mini chocolate chips if desired.
Recipe from The Baking Chocolatess