Ridiculously Good Rolo Cookies

Rolo cookiesI was craving something chocolately and chewy, so I went through some of my cookbooks and binder of recipes cut out of newspapers and magazines, and settled upon these cookies. All I have to say is: O…M…G…THESE ARE GOOD, and by good I mean really super good and are now going to be regulars in my arsenal good.  

Warning: they need time to chill twice, so keep that in mind when going to make them (unlike myself that made them after dinner and had to wait 2.5 hours for cookies/dessert!).

Rolo Cookies


  • 2½ cups flour
  • ¾ cup cocoa
  • 1 teaspoon baking soda
  • 1 cup white sugar
  • 1 cup firmly packed brown sugar
  • 1 cup butter, softened
  • 2 teaspoons vanilla
  • 2 eggs
  • 70 to 75 Rolo candies (7 to 8 packages)


Combine flour, cocoa and baking soda with a whisk in a medium bowl.

In a separate bowl, beat sugar and butter. Add vanilla and eggs. Stir in flour/cocoa mixture until well combined. Then chill dough for 1 hour.

Shape about 1½ teaspoons of dough around a Rolo, making sure it is completely covered. Place on ungreased cookie sheet and chill for 1 more hour.

About half way to most of the way through the second cooling, depending on your oven, preheat your oven to 375oF. Bake cookies for 7 to 8 minutes. Cool on wire rack before storing.

Note: this recipe makes between 70-75 cookies, so I halfed it. But, they make small cookies, so 75ish isn’t as crazy of an amount as it seems. Also, I would definitely recommend heating them up for 10-20 seconds (depeding on the microwave) before eating, somehow makes them even better!


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