There’s just something about fall that puts me in the baking mood -plus, I’m pretty sure the Cookie Monster and I have some type of genetic connection. I have always loved playing around with the notion of combining cookies and candies. A few years back, my friend brought some cookies stuffed with rolos to a cookie exchange. She never gave me the recipe, so I’ve played around a bit with my basic chocolate cookie recipe, and came up with these.

They are SOFT, chewy, and have a tasty little Rolo inside. Does it get better than a soft chocolate cookie with a bit of gooey caramel inside?

rolo cookies


3/4 c. butter

1/2 c. shortening

2 cups granulated sugar

2 eggs

2 tsp. vanilla extract

3 c. all-purpose flour

3/4 c. cocoa powder

1 tsp. baking soda

1 tsp. corn starch

1/2 tsp. salt

24 mini Rolo candies (You can use the regular size, but the minis are easier to fit inside a cookie, and come unwrapped!)

To Prepare

1. Preheat your oven to 350 degrees.

2. Cream together the butter, shortening, and sugar. Add eggs and vanilla, and mix well.

3. Add in the flour, cocoa powder, salt, baking soda, and corn starch. (If using a mixer, make sure you start out on a SLOW speed – or you’ll soon be covered in a chocolatey-floury mess!)

4. Scoop out your dough onto a cookie sheet. (I always use my Pampered Chef cookie scoop.) Press one mini Rolo into the center of each ball of dough. Gently cover the top of the Rolo with the dough, so that it is fully covered.

5. Bake about 9-10 minutes. (Oven times and temps will vary, so keep a  watchful eye.) Pull these out when they are slightly under-baked, and allow them to finish baking on the sheet, outside of the oven for several minutes, before transferring to a wire cookie rack.

Enjoy these soft and ooey-gooey chocolate and caramel cookies! You’ll love them!


Like Cookies? You May Also Like:

Soft and Chewy Reese’s Pieces Fall Cookies









Oatmeal Raisinet Cookies

oatmeal cookies








Peanut Butter Cookie Dough Brownies

Peanut Butter Cookie Dough Brownies








Chasing Supermom’s Snickerdoodles