Oreo Cinnamoon Roolls

These decadent Oreo Cinnamon Rolls combine two beloved treats into one showstopping birthday dessert that's perfect for a special celebration like Phil's birthday. A medium-difficulty recipe that rewards attention to detail, these indulgent rolls feature soft, fluffy dough swirled with a buttery cinnamon-sugar filling that's studded with crushed Oreo cookies, then topped with a luscious cream cheese frosting infused with more Oreo goodness. Each bite delivers the perfect balance of warm, comforting cinnamon spice paired with rich chocolate cookie chunks and sweet vanilla cream filling, creating a truly unforgettable birthday breakfast or dessert that looks as impressive as it tastes.

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Oreo Cinnamoon Roolls - main view
Chef profile

JUE

Enjoy home-cooked meals made with love and shared from a family kitchen.

Chef's Essential Tips

Essential Ingredients Selection

Creating Your Masterpiece

Oreo Cinnamoon Roolls - secondary view

Crafting the Ultimate Beverage

Base Preparation:
Begin by blending fresh fruits, yogurt, and honey until smooth. The mixture should have a creamy texture.
Flavor Infusion:
Slowly add spices or herbs of your choice, ensuring even distribution. This step enhances the depth of flavor.
Base Preparation:
Begin by blending fresh fruits, yogurt, and honey until smooth. The mixture should have a creamy texture.
Flavor Infusion:
Slowly add spices or herbs of your choice, ensuring even distribution. This step enhances the depth of flavor.
Base Preparation:
Begin by blending fresh fruits, yogurt, and honey until smooth. The mixture should have a creamy texture.
Baking Tips
For the fluffiest rolls, make sure your milk is at the right temperature (110°F/43°C) - too hot and it will kill the yeast, too cool and the yeast won't activate properly
Let the dough rise in a warm, draft-free area. A slightly warmed (then turned off) oven or an oven with just the light on works well
For cleaner cuts, use unflavored dental floss instead of a knife to slice the roll - slide the floss under the roll, cross it over the top, and pull
Don't skip pouring the heavy cream over the rolls before baking - this creates an incredibly tender, moist texture
To make ahead: Prepare the rolls up to the point of the second rise, then cover tightly and refrigerate overnight. In the morning, let them come to room temperature for 30-45 minutes before baking
For extra birthday flair, add a few drops of food coloring to the frosting to create Phil's favorite color
Leave the cream cheese and butter for the frosting out at room temperature for at least an hour before making the frosting for the smoothest consistency
For a stronger Oreo flavor, use double-stuffed Oreos
When crushing the Oreos, it's okay to leave some larger chunks for texture and visual appeal
For a special touch, write 'Happy Birthday Phil' on the top using melted chocolate
Oreo Cinnamoon Roolls - tertiary view

Oreo Cinnamoon Roolls

These decadent Oreo Cinnamon Rolls combine two beloved treats into one showstopping birthday dessert that's perfect for a special celebration like Phil's birthday. A medium-difficulty recipe that rewards attention to detail, these indulgent rolls feature soft, fluffy dough swirled with a buttery cinnamon-sugar filling that's studded with crushed Oreo cookies, then topped with a luscious cream cheese frosting infused with more Oreo goodness. Each bite delivers the perfect balance of warm, comforting cinnamon spice paired with rich chocolate cookie chunks and sweet vanilla cream filling, creating a truly unforgettable birthday breakfast or dessert that looks as impressive as it tastes.

Italian Cream Stuffed Cannoncini
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Ingredients

Custard Cream
01
For the Dough:
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1 cup whole milk, warmed to 110°F (43°C)
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2 1/4 teaspoons (1 packet) active dry yeast
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1/2 cup granulated sugar, divided
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1/3 cup unsalted butter, softened
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2 large eggs, room temperature
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1 teaspoon vanilla extract
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1 teaspoon salt
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4 to 4 1/2 cups all-purpose flour, plus more for dusting
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For the Filling:
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1/2 cup unsalted butter, softened
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1 cup light brown sugar, packed
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2 tablespoons ground cinnamon
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20 Oreo cookies, crushed (about 2 cups), divided
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1/4 cup heavy cream (for pouring over rolls before baking)
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For the Cream Cheese Frosting:
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8 oz cream cheese, softened
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1/4 cup unsalted butter, softened
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2 cups powdered sugar
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1 teaspoon vanilla extract
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2-3 tablespoons milk or heavy cream
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10 Oreo cookies, crushed (about 1 cup), divided
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For Decoration:
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6 whole Oreo cookies, for topping
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Chocolate sauce, for drizzling (optional)
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Birthday candles (for Phil!)
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Equipment:
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Stand mixer with dough hook (or large bowl if mixing by hand)
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Large mixing bowls
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Rolling pin
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9x13 inch baking dish
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Measuring cups and spoons
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Plastic wrap
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Food processor or zip-top bag (for crushing Oreos)
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Electric mixer for frosting
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Offset spatula

Instructions

01
For the dough: In the bowl of a stand mixer, combine warm milk, 1 tablespoon of the sugar, and yeast. Let sit for 5-10 minutes until foamy and activated.
02
Add the remaining sugar, softened butter, eggs, vanilla extract, and salt to the yeast mixture. Mix on low speed until combined.
03
Gradually add 4 cups of flour, 1 cup at a time, mixing on low speed until incorporated. The dough should pull away from the sides of the bowl but still be slightly sticky. Add additional flour if needed, 1 tablespoon at a time.
04
Switch to the dough hook attachment and knead on medium-low speed for 5-7 minutes until the dough is smooth and elastic. Alternatively, turn dough out onto a floured surface and knead by hand.
05
Place dough in a large greased bowl, cover with plastic wrap or a clean kitchen towel, and let rise in a warm place for 1-1.5 hours, until doubled in size.
06
While the dough rises, prepare the filling: In a food processor, pulse 15 Oreo cookies until coarsely crushed, leaving some chunks for texture. Set aside. Keep remaining 5 crushed Oreo cookies separate for sprinkling on the rolled dough.
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In a medium bowl, mix together the softened butter, brown sugar, and cinnamon until well combined. Fold in the 15 crushed Oreo cookies. Set aside.
08
Once the dough has doubled in size, punch it down to release air bubbles. Turn it out onto a lightly floured surface and roll into a large rectangle, approximately 18x12 inches.
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Spread the Oreo-cinnamon-sugar mixture evenly over the dough, leaving a 1/2-inch border around the edges. Sprinkle the remaining 5 crushed Oreo cookies evenly over the filling.
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Starting from one of the long edges, tightly roll the dough into a log. Pinch the seam to seal.
11
Using a sharp knife or unflavored dental floss, cut the log into 12 equal pieces, each about 1.5 inches thick.
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Place the rolls in a greased 9x13 inch baking dish, spacing them evenly. Cover and let rise for another 30-45 minutes, until puffy.
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Preheat the oven to 350°F (175°C). Once rolls have risen, pour the heavy cream evenly over the rolls.
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Bake for 22-25 minutes, until the rolls are golden brown and cooked through. The internal temperature should reach approximately 190°F (88°C).
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While the rolls are baking, prepare the frosting: In a large bowl, beat cream cheese and butter until smooth and fluffy. Add powdered sugar gradually, beating on low speed until incorporated. Mix in vanilla extract and enough milk or cream to reach desired consistency.
16
Fold 3/4 cup of the crushed Oreos into the frosting, saving the remaining 1/4 cup for topping.
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When the rolls come out of the oven, let them cool for about 10 minutes before spreading the Oreo cream cheese frosting generously over the warm rolls.
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Sprinkle the remaining 1/4 cup crushed Oreos over the frosted rolls. Place whole Oreo cookies decoratively on top and drizzle with chocolate sauce if desired.
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For Phil's birthday celebration, arrange birthday candles on top right before serving.
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Serve warm for the best experience. These rolls can be prepared the night before and refrigerated before the second rise for a special birthday breakfast.