One of my friends was asking about Rolo stuffed cookies. I had made them before & gave her a link to someone who had blogged the recipe.

Then I got to thinking of doing my own Rolo stuffed cookie, but instead of the traditional chocolate cake mix cookie, I would do a Rolo stuffed snickerdoodle. I am on a caramel kick & that sounded wonderful to me. So here they are! And they are amazing!

Rolo Stuffed Snickerdoodles

Rolo Stuffed Snickerdoodles


  • 1/2 cup (1 stick) of butter, room temperature
  • 3/4 cup sugar
  • 1 egg
  • 1/2 tsp vanilla
  • 1 1/4 cup + 2 Tbsp flour
  • 1 tsp cream of tartar
  • 1/4 tsp salt
  • 1/2 tsp baking soda
  • 24 Rolo Chocolates, unwrapped
  • 2 Tbsp sugar
  • 3/4 tsp cinnamon


  1. In a stand mixer, cream butter with ¾ cup sugar. Add egg & vanilla & mix thoroughly.
  2. Add flour, cream of tartar, salt & baking soda. Mix until incorporated.
  3. In a separate small bowl, combine 2 Tbsp sugar with ¾ tsp cinnamon. Set aside.
  4. Scoop some cookie batter, squish a Rolo in the center, pinch & smooth any seams by rolling the dough in your hands, hiding the rolo in the middle. Then roll cookie ball into cinnamon sugar mixture. (I use a #50 cookie scoop.) Place on a greased cookie sheet & repeat for all cookies.
  5. Bake at 325*F for 12-13 minutes.