Tootsie Roll Cookies

Tootsie Roll Cookies


  • 1/3 + 1 tablespoon cup unsalted butter, softened
  • 1/2 cup Imperial Sugar Extra Fine Granulated Sugar
  • 1/2 cup Imperial Sugar Light Brown Sugar
  • 1 large egg
  • 1 tablespoon vanilla extract
  • 1 cup all-purpose flour*
  • 1/2 cup cocoa powder
  • 1/2 teaspoons baking soda
  • 1/2 teaspoon salt
  • 20 Tootsie Roll® Midgees, unwrapped
  • 2 tablespoons whole milk or heavy cream
  • 1 tablespoon sea salt for garnish if desired
  • *Spoon & Sweep method: Use a spoon to fill measuring cup with flour until required amount is obtained. Scooping measuring cup directly into flour bag will firmly pack flour resulting in too much flour required for recipe.


  1. Preheat oven to 350°F.
  2. In mixer, cream together butter and both sugars.
  3. Add egg and vanilla. Mix well.
  4. In a large bowl, whisk together flour, cocoa powder, baking soda, and salt.
  5. With mixer on low, slowly add flour mixture to batter. Mix until just combined.
  6. Drop by leveled 1 tablespoon scoops onto a baking sheet.
  7. Slightly press cookie down and use thumb or back of 1/2 tablespoon measuring spoon to create a well in middle of dough.
  8. Bake for 7-8 minutes.
  9. Remove from oven and use back of 1/2 tablespoon measuring spoon to press down middle of cookie again.
  10. While cookies are cooling, add Tootsie Roll Midgees and milk to small sauce pan. Melt and stir Tootsie Roll Midgees over medium heat until smooth.
  11. Fill centers of cookies with Tootsie Roll Midgees ganache.
  12. Sprinkle with sea salt if desired.
  13. Let cool.
Imperial Sugar Insight

Recipe developed for Imperial Sugar by Angie Barrett @BigBearsWife.

Rate & Review
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Sweetalk member
Dec 20, 2020

The proportions on this recipe were off. I measured everything carefully. I ended up with 35 cookies. I baked at the correct temperature. At 8 minutes they were no where close to done. At 10-11 minutes they had risen nicely and I took them out. I used a spoon to make the indentations - it was basically collapsing the structure. When they cooled they were completely flat. I had made the tootsie roll ganache by this time so I just drizzled it across the tops. The cookies are cool but still much too soft to support the ganache, if you pick up a cookie, it just bends.. I think the flour probably needs to be doubled. They taste okay.

The tootsie roll ganache is good - I like the ganache way better than tootsie rolls..

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