Cookies and Cream OREO Rolls

Soft and fluffy Oreo Rolls made with crushed OREO cookies, buttery dough, and a smooth cookies-and-cream frosting. Perfect for special mornings, holidays, or dessert.

Prep Time 30

Cook Time 25

Rise Time 1 30

Servings rolls

Calories/serving 353 kcal

Ingredients

OREO roll dough:

▢ 1 cup warm milk whole or 2%
▢ 2 Tablespoons +1 teaspoon sugar divided
▢ 2 ¼ teaspoons quick rise yeast 1 packet
▢ 6 Tablespoons butter mostly melted, I used salted
▢ 1 large egg at room temperature, whisked
▢ 1 teaspoon salt
▢ 3-31/4 cups bread flour or all purpose flour, see note 1

OREO roll Filling:

▢ ¼ cup butter very very soft
▢ ⅓ cup sugar
▢ ¼ cup brown sugar
▢ 1 ¼ cups crushed OREOs about 10-12

Cookies and Cream Roll Frosting:

Instructions

Make the dough:

Combine warm milk (105-110° F) and combine with the yeast and 1 teaspoon of the sugar. Set aside to proof for 5 minutes. Within 5 minutes the mixture should be very foamy and growing pretty rapidly. If not, throw away and start over. Your yeast must be active and well for the best cinnamon rolls.
Microwave the butter until partially melted and whisk the egg. Combine butter, egg, salt, sugar, salt, remaining sugar, bread flour and proofed yeast together and mix to combine. You can use a stand mixer with a dough hook attachment, your hands (I recommend watching a youtube video on how to knead if you do this by hand) or a bread maker on the dough setting to knead the dough. Knead 10-20 minutes until dough is elastic and silky smooth. Push a finger into the dough to make an indentation; the dough should bounce back easily. See photos above for a visual guide.
Spray a glass or plastic bowl with cooking spray or oil it with your preferred oil. Place dough inside, then spray the top with a little oil so it doesn't dry out. Cover with cling wrap and allow to rise in a warm place until doubled in size, about an hour.

Make Filling and Form Rolls:

Combine the sugar, brown sugar and crushed OREOs together in a bowl.
Roll the dough out evenly. Form into a rectangle that's roughly 12"x18". Spread the very soft butter across the dough evenly. Sprinkle the OREO cookie sugar mixture evenly over top of the butter.
Starting on the long end, roll up the dough. Cut into 12 even rolls, see note 2 for suggestions for making them even. Place evenly in a greased or parchment lined 9x13" pan. I like to spread them out a bit and make sure they aren't tightly rolled. I find this enables the insides of the rolls to puff up and expand more. Cover and allow to rise for 30 minutes. 10 minutes in, preheat the oven to 350° F. Once they are done rising, bake for 17-22 minutes until done. The tops and edges will just be starting to turn golden brown.

Frosting:

Beat the butter on medium high speed until no lumps remain. Add the cream cheese and beat together on medium speed until completely smooth and lump free, about 1-2 minutes. Add the powdered sugar and mix until well combined. Add the vanilla, then mix until combined. Crush about 4 OREOs.
Allow cinnamon rolls to cool about 10-15 minutes before frosting. This way they will still be warm and the icing will seep into the rolls. For frosting that sits on top of the rolls, wait until they have cooled completely. After frosting the rolls, sprinkle the OREO pieces on top, serve and enjoy! Make sure to check out the notes below for all the tips and tricks!

Notes

You can make these with all-purpose flour and they'll turn out fine. Bread flour makes them more tender as well as helps them stay soft and moist longer.
I like to cut the log in half, then each half in half again. Then each of those I cut into 3 even pieces. This is the easiest way for me to get them even in size. See picture above for a visual reference.
These are best served warm and fresh! For cookies and cream rolls that are a day or 2 old, we highly recommend microwaving for 10-20 seconds before enjoying for the soft, tender, just out of the oven feel!
Loosening the rolls a little bit when I put them into the pan helps them expand and the middles to be more fluffy and less dense.
These can be made with 1% or skim milk, if desired. Using a higher fat milk like whole or 2% will result in a more tender roll.

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