Chocolate Rolo Cookies

Cookie Prep Station

When I was growing up in Quebec, Caramilk chocolate bars were some of my favorite. Basically Cadbury chocolate with gooey caramel inside – yum! When we moved to the US in 1985, Rolos were as close as it got and I began enjoying them almost as much as my beloved Caramilks.

Rolo In Cookie Dough

When this year’s The Great Food Blogger Cookie Swap came along, I knew I wanted to stuff a Rolo inside a chocolate cookie as my entry. Chocolate, caramel…need I say more?

This recipe yields 4 dozen cookies, perfect for the three dozen I needed to ship to my matches and a dozen for moi!

Ingredients:

• 2 sticks (1 cup) butter, softened
• 1 cup light brown sugar
• 1 cup granulated sugar
• 2 large eggs
• 2 tsp. pure vanilla extract
• 2 ½ cups all-purpose flour
• 1 tsp. baking soda
• ¼ tsp. Kosher salt
• ¾ cup unsweetened cocoa powder
• 48 Rolos, unwrapped
• ½ cup granulated sugar

Cookie Dough Balls

Directions:

1. Preheat oven to 375 degrees F.
2. Line two cookie sheets with parchment paper.
3. In the bowl of an electric mixer, cream the butter with the brown sugar and the cup of granulated sugar until light and fluffy, about 3 minutes. Add the eggs, one at a time, and the vanilla. Beat until just combined.
4. Sift the flour, baking soda, salt and cocoa in a medium bowl. Add the flour mixture, ¼ cup at a time, to the butter/sugar mixture until fully incorporated – don’t overmix.
5. 

   Baked Cookies

   Take a teaspoon of cookie dough and flatten it in your hand or on the counter. Wrap the flatten cookie dough around a Rolo. Once you’ve ensured the Rolo is covered completely with the cookie dough, roll the dough ball in the remaining sugar and place on the prepared baking sheets – 12 cookies per sheet. Roll the remaining 2 dozen cookies and set aside.

6. Bake the first 24 cookies for 8-10 minutes. Remove from the oven and allow to cool for 5 minutes on the sheets then move to a cookie rack to cool completely. Repeat with the remaining 2 dozen cookies.

Yields 4 dozen cookies.

Inspired by Two Peas & Their Pod