
Oreo cinnamon rolls transform the familiar comfort of traditional breakfast pastry into something truly extraordinary. The marriage between classic cinnamon rolls and beloved chocolate sandwich cookies creates an indulgent experience that satisfies multiple cravings simultaneously. Each bite delivers that perfect gooey, sweet cinnamon sugar base we all love while introducing rich chocolate depth and distinctive cookie crunch. The contrast between the fluffy, tender dough and the chocolate cookie filling creates a textural playground, all crowned with silky vanilla frosting that melts perfectly into the warm rolls.
The first time I made these for Sunday brunch, my kitchen became the most popular room in the house. Family members who typically sleep until midday suddenly appeared, drawn by the intoxicating aroma of baking cinnamon and chocolate.
Roll Essentials
- 1 cup warm milk: Activates the yeast while adding richness to the dough.
- 2¼ teaspoons active dry yeast: Creates a perfectly fluffy texture.
- ½ cup granulated sugar: Feeds the yeast while balancing chocolate flavors.
- ⅓ cup unsalted butter, softened: Enriches the dough for a melt-in-your-mouth quality.
- 2 large eggs, room temperature: Provide structure and richness.
- 1 teaspoon salt: Enhances all other flavors.
- 4½ cups bread flour: Creates the perfect chewy yet tender structure.
- ½ cup butter, softened for filling: Allows for easy spreading.
Chocolate Cookie Filling
- 1 cup packed brown sugar: Adds caramelized sweetness.
- 3 tablespoons ground cinnamon: Provides warm spice depth.
- 3 tablespoons black cocoa powder: Delivers the signature Oreo cookie flavor.
- 2 cups finely crushed Oreo cookies: Infuses authentic cookie flavor and texture.
Vanilla Frosting
- 4 ounces cream cheese, softened: Creates the perfect creamy base.
- ¼ cup unsalted butter, softened: Adds richness and silky texture.
- 2 cups powdered sugar: Sweetens while creating proper consistency.
- 2 tablespoons milk: Adjusts thickness for spreading.
- 1 teaspoon pure vanilla extract: Balances the sweetness.
- Additional crushed Oreos for garnish: Enhances visual appeal and flavor.
Baking Process
- Activate Your Yeast:
- Combine warm milk, sugar, and yeast. Let sit for 10-15 minutes until foamy.
- Create Your Dough Base:
- Add softened butter, eggs, and salt. Gradually incorporate flour while mixing.
- Develop The Structure:
- Knead dough until soft and slightly tacky.
- Allow Primary Fermentation:
- Let dough rise in a greased bowl for 1½ hours until doubled.
- Form Your Rolls:
- Roll dough into a 14x18-inch rectangle, spread butter, and sprinkle filling mixture evenly.
- Create The Spiral:
- Roll dough tightly into a log and slice into 12 portions.
- Secondary Fermentation:
- Let shaped rolls rise for 45-60 minutes until puffy.
- Bake To Perfection:
- Bake at 375°F for 14-18 minutes until golden brown.
- Finish With Frosting:
- Spread vanilla frosting over warm rolls and garnish with crushed Oreos.

My journey with these Oreo cinnamon rolls began during a weekend baking session with my teenage niece, who constantly seeks ways to incorporate her favorite cookies into everything.
Texture Perfection
Proper kneading develops the gluten structure needed for tender yet structured rolls. The perfect dough should stretch into a translucent windowpane without tearing.
Flavor Balancing
The Oreo flavor comes primarily from black cocoa powder, which creates a deep chocolate taste. Vietnamese or Ceylon cinnamon adds complexity to balance the chocolate.
Serving Suggestions
Pair with vanilla bean ice cream for an indulgent dessert. Coffee with chocolate undertones enhances the experience, while a toppings bar allows customization.
Make-Ahead Magic
Refrigerate unbaked rolls overnight or freeze for up to three months. Let thaw before baking. Prepare frosting ahead and rewhip before spreading.

Developing these Oreo cinnamon rolls taught me that playful experimentation often leads to the most delightful creations. Watching faces light up with the first bite is the ultimate baking reward.
Frequently Asked Questions
- → What is black cocoa powder and where can I find it?
- Black cocoa powder is an ultra-Dutch processed cocoa that gives Oreo cookies their distinctive flavor and color. It's darker and less bitter than regular cocoa powder, with that classic cookies-and-cream taste. You can find black cocoa powder online through specialty baking stores or Amazon. If you can't find it, you can substitute regular Dutch-processed cocoa powder, though the flavor won't be exactly the same - add an extra tablespoon of crushed Oreos to compensate.
- → Can I make these Oreo Cinnamon Rolls ahead of time?
- Absolutely! These Oreo Cinnamon Rolls are perfect for preparing ahead. After cutting the rolls and placing them in the baking pan, cover with plastic wrap and refrigerate overnight. The next morning, let them sit at room temperature for about 45 minutes (they may not look very puffy, and that's okay), then bake as directed. The slow rise in the refrigerator actually enhances the flavor development, making this a great option for holiday or weekend breakfasts without the early morning work.
- → How can I tell when my dough has risen enough?
- For Oreo Cinnamon Rolls, the dough should roughly double in size during both rising periods. For the first rise in the bowl, the dough should look noticeably larger and feel soft and puffy when gently poked. During the second rise after shaping, the rolls should expand to fill the pan and press against each other. A good test is the poke test - press your finger gently into the dough about half an inch, and if the indentation slowly fills back about halfway, the dough is ready to bake.
- → Can I freeze these cinnamon rolls?
- Yes, Oreo Cinnamon Rolls freeze beautifully. You have two options: freeze them before baking (after cutting and placing in the pan), or freeze them after baking but before frosting. For unbaked rolls, thaw overnight in the refrigerator, then allow to come to room temperature for about an hour before baking. For baked rolls, thaw at room temperature, then warm in a 300°F oven for 10-15 minutes before adding frosting. Either way, they'll keep in the freezer for up to a month when wrapped properly.
- → Why didn't my rolls rise properly?
- If your Oreo Cinnamon Rolls didn't rise well, there are a few possible culprits. First, check that your yeast is fresh - expired yeast won't activate properly. Second, the liquid used to bloom the yeast should be warm (105-110°F), not hot, as high temperatures kill yeast. Third, rising environments matter - for sluggish dough, create a warm spot by preheating your oven for just a minute, turning it off, then placing the covered dough inside. Finally, be patient - rising times are estimates, and cooler kitchens require longer proofing periods.