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Cookies and Cream Cinnamon Rolls

A close-up of a warm, gooey cookies and cream cinnamon roll topped with white frosting and crushed cookies.

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Indulgent bakery-style cinnamon rolls with a chocolate sandwich cookie filling and cream cheese frosting, perfect for a weekend brunch.

Ingredients

Scale
  • 1 cup warm milk (105-115°F)
  • 2 ¼ teaspoons active dry yeast
  • ½ cup granulated sugar
  • 1 teaspoon salt
  • 2 large eggs, room temperature
  • ½ cup unsalted butter, melted
  • 4 ½ cups all-purpose flour, plus more for dusting
  • 1 cup finely crushed chocolate sandwich cookies (about 10 cookies)
  • ½ cup packed light brown sugar
  • 2 teaspoons ground cinnamon
  • ½ cup unsalted butter, softened
  • 8 ounces cream cheese, softened
  • 1 cup powdered sugar
  • 1 teaspoon vanilla extract
  • 24 tablespoons milk

Instructions

  1. In a large bowl, combine warm milk and yeast. Let sit for 5-10 minutes until foamy.
  2. Stir in granulated sugar, salt, eggs, and melted butter.
  3. Gradually add flour, mixing until a soft dough forms. Knead on a floured surface for 8-10 minutes until smooth and elastic.
  4. Place dough in a greased bowl, cover, and let rise in a warm place for 1-1.5 hours, or until doubled in size.
  5. Punch down dough and roll into a 12×18 inch rectangle on a floured surface.
  6. Spread softened butter evenly over the dough, leaving a ½ inch border.
  7. In a small bowl, mix crushed cookies, brown sugar, and cinnamon. Sprinkle evenly over the buttered dough.
  8. Starting from a long edge, tightly roll up the dough. Pinch the seam to seal.
  9. Cut the roll into 12 equal slices.
  10. Place slices in a greased 9×13 inch baking pan. Cover and let rise for 30-45 minutes.
  11. Preheat oven to 350°F (175°C).
  12. Bake for 20-25 minutes, or until golden brown.
  13. While rolls bake, prepare frosting: Beat cream cheese until smooth. Add powdered sugar and vanilla, beating until combined. Gradually add milk until desired consistency is reached.
  14. Let rolls cool slightly before spreading frosting over the top.

Notes

  • For overnight rolls, prepare through step 8, cover tightly, and refrigerate. In the morning, let sit at room temperature for 30 minutes before baking as directed.
  • Use a serrated knife for clean cuts when slicing the dough.
  • Ensure your cream cheese and butter are fully softened for the smoothest frosting.

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