Cookies and cream cinnamon rolls are filled with crushed Oreo cookies and gooey cinnamon filling, topped with rich cream cheese frosting. They're easy to assemble and make the perfect weekend treat!
Lightly grease a 9x9 square baking dish or 9-10 inch round cake or pie pan and set aside.
In a large bowl, add flour, cocoa powder, granulated sugar, and salt. Whisk to combine. Set aside.
In a microwave safe bowl, add milk and butter. Microwave in 20 second increments until butter has melted and mixture is warm to the touch, but not hot (about 110 degrees Fahrenheit).
Whisk in yeast and continue whisking until yeast has dissolved. Pour yeast mixture into dry ingredients. Add the egg and stir with a sturdy wooden spoon until a soft dough forms.
Turn dough out onto a lightly floured surface. Using floured hands, knead the dough for 3 to 5 minutes, or until dough looks smooth (not sticky).
Transfer dough to a lightly greased bowl, lightly cover, and allow to rise for 10 minutes.
Filling
Roll dough out on a lightly floured surface into a 14x9 rectangle.
Spread room temperature butter evenly across the dough. In a small bowl, combine brown sugar and cinnamon, then sprinkle evenly over the butter. Top with chopped Oreo cookie pieces.
Starting at the long 14 inch side, roll dough up into a log. Using a serrated knife, slice into 9 even rolls and place into prepared baking dish.
Lightly cover and allow rolls to rise at room temperature for 60-90 minutes, or until they've doubled in size.
Preheat oven to 350℉.
Transfer dish to the oven and bake, uncovered, for 26-30 minutes, or until golden brown across the top and rolls reach 195-200 degrees Fahrenheit in the center (use an instant read thermometer to test internal temperature). If rolls are browning too quickly, lightly tent with foil for the remaining baking time.
While the rolls bake, prepare the frosting.
Frosting
In a medium bowl, add cream cheese and butter. Using a hand mixer or stand mixer, beat until creamy and smooth. Add confectioner's sugar and vanilla extract and mix until combined.
Using a knife, spread frosting over warm cinnamon rolls, top with chopped Oreo cookies, and serve immediately. Alternatively, use a pastry bag to pipe frosting on top.
Notes
Overnight directions: After assembling the rolls, cover and transfer to the refrigerator to rise overnight (this replaces the 60-90 minute rise). In the morning, remove cinnamon rolls from the refrigerator and uncover while the oven preheats. Bake as directed in the recipe card above.
Leftovers: Store leftover frosted cinnamon rolls in the refrigerator for 4-5 days. Unfrosted rolls can be stored at room temperature for 2-3 days.
Freezing baked rolls: Baked cinnamon rolls freeze well and keep for up to 3 months.
Freezing unbaked cinnamon rolls: Follow the directions above for assembly and rising, using a disposable foil pan (or other freezer-safe pan you don't mind freezing for a while). Bake your cinnamon rolls at 350F for 10 minutes. They should look risen and par-cooked, but not yet browned. Cool completely, then cover tightly and freeze for up to 3 months. Transfer to the refrigerator to thaw overnight. In the morning, preheat your oven to 350F and bake for the remaining 16-20 minutes.