Decadent Oreo-Stuffed Cinnamon Rolls with Cream Cheese Glaze

Introduction & Inspiration

Get ready for a cinnamon roll experience unlike any other! These Oreo-Stuffed Cinnamon Rolls take the beloved classic to a whole new level of decadence and fun. Imagine a soft, fluffy, homemade yeast dough, generously spread with butter and a warm cinnamon-sugar mixture. But here’s the exciting twist: nestled along the edge before rolling is a row of whole Oreo cookies! When baked, they soften into a delightful chocolatey-creamy layer within the cinnamon swirl. Topped with a tangy, sweet cream cheese glaze and optional crushed Oreos, these rolls are pure, indulgent bliss.

My inspiration for this recipe comes from the sheer joy of combining two ultimate comfort treats: warm, gooey cinnamon rolls and iconic Oreo cookies. I wondered how amazing it would be to find that surprise Oreo inside, and the result is a playful, over-the-top breakfast pastry or dessert that’s guaranteed to delight.

These rolls are perfect for a special weekend brunch, a celebratory breakfast, or anytime you want to treat yourself and your loved ones to something truly spectacular. They are a bit of a project, but oh-so-worth it! This is a perfect recipe for Oreo lovers.

Nostalgic Appeal / Comfort Factor

Warm, gooey cinnamon rolls are the epitome of nostalgic comfort food, evoking feelings of cozy weekend mornings, holiday breakfasts, and the irresistible aroma of cinnamon and yeast baking. Oreo cookies are another powerhouse of nostalgia, a beloved childhood favorite known for that classic cookies-and-cream flavor.

This recipe brilliantly fuses these two comfort food giants. You get the soft, pillowy texture and warm spice of a classic cinnamon roll, with the exciting surprise and familiar taste of an Oreo cookie baked right inside. The cream cheese glaze adds another layer of comforting richness and tang.

It’s a fun, indulgent mashup that delivers an extra dose of happy nostalgia and satisfying sweetness. A perfect comfort food treat.

Homemade Focus

This recipe is a wonderful celebration of homemade baking from scratch, particularly the satisfying process of working with yeast dough. You’ll be creating the soft, pliable dough yourself, kneading it to develop that perfect texture, and allowing it to rise. The cinnamon-sugar filling and the creamy cheese glaze are also homemade.

The unique homemade aspect here is the clever incorporation of whole Oreo cookies into the roll before slicing and baking. This technique, along with carefully rolling and cutting the dough, showcases the craft of homemade sweet rolls.

Making these entirely from scratch allows you to experience the magic of yeast dough and create a truly special, multi-component treat with superior flavor and texture. The homemade taste is incredible.

Flavor Goal

The primary flavor goal is a harmonious blend of warm cinnamon-sugar, rich yeasty dough, the distinct chocolatey and creamy flavor of Oreo cookies, and a tangy-sweet cream cheese glaze.

The dough itself should be soft, fluffy, and slightly sweet. The cinnamon-sugar filling, combined with the softened butter, should create gooey, sweet, spiced swirls. The Oreo cookie, softened during baking, should provide a distinct layer of chocolate cookie and cream filling within the roll. The cream cheese glaze adds a final touch of tangy sweetness and creamy richness.

The overall experience should be a decadent, multi-textured, and multi-flavored roll that perfectly combines the best of cinnamon rolls and Oreos. A perfect balance between flavour and texture.

Ingredient Insights

(Estimated Quantities for 9-12 Rolls)

For the Dough:

• All-Purpose Flour: Provides structure. About 3 to 3 ½ cups.
• Granulated Sugar: Sweetens the dough and feeds the yeast. About 1/4 to 1/2 cup.
• Instant or Active Dry Yeast: The leavening agent. About 2 ¼ teaspoons (1 standard packet). If using active dry, proof it first in some of the warm liquid with a pinch of sugar.
• Salt: Balances flavor and controls yeast activity. About 1 teaspoon.
• Warm Milk & Warm Water: Activates the yeast and hydrates the dough. Temperature should be lukewarm (105-115°F for active dry yeast). About 1/2 cup milk and 1/4 cup water.
• Large Egg: Adds richness, structure, and binding. Room temperature.
• Melted Butter: Adds flavor and tenderness to the dough. About 1/4 cup.

For the Oreo & Cinnamon Filling:

• Softened Butter: Spread over the rolled-out dough to help the cinnamon-sugar adhere and add richness. About 1/4 to 1/2 cup.
• Brown Sugar & Granulated Sugar: Creates the sweet, gooey filling. A mix provides good flavor. About 1/2 – 3/4 cup total.
• Ground Cinnamon: The essential warm spice. About 1-2 tablespoons.
• Oreo Cookies: Whole Oreo cookies (standard stuff) are placed in a row before rolling. About 10-15 cookies, depending on log length.

For the Cream Cheese Glaze:

• Cream Cheese (Softened): Provides the tangy, creamy base. Full-fat, brick-style, properly softened. About 4-8 oz.
• Butter (Softened): Adds richness and smoothness to the glaze. About 2-4 tablespoons.
• Powdered Sugar (Sifted): Sweetens and thickens the glaze. About 1-2 cups.
• Vanilla Extract: Essential flavor for the glaze. About 1 teaspoon.
• Milk or Cream (Optional): To adjust glaze consistency.

Garnish (Optional):

• Crushed Oreos: For sprinkling on top of the glaze.

Essential Equipment

• Large Mixing Bowl (or Stand Mixer with Dough Hook): For making the yeast dough.
• Plastic Wrap or Clean Kitchen Towel: For covering dough during rising.
• Rolling Pin: To roll out the dough into a rectangle.
• Lightly Floured Surface: For kneading and rolling dough.
• Sharp Knife or Unflavored Dental Floss: For slicing the log into individual rolls cleanly.
• Greased Baking Dish (e.g., 9×13 inch or 2 round 9-inch pans): For the second rise and baking.
• Small Bowl: For cinnamon-sugar filling.
• Medium Bowl & Electric Mixer (Handheld or Stand): For making the cream cheese glaze.
• Measuring Cups & Spoons:
• Spatula: For spreading butter/filling and glaze.
• Wire Cooling Rack:

Ingredients

(Estimated Standard Quantities for 9-12 Rolls)

For the Dough:

• ▢ 3 – 3 ½ cups all-purpose flour
• ▢ ¼ cup granulated sugar
• ▢ 2 ¼ teaspoons instant yeast (1 packet)
• ▢ 1 teaspoon salt
• ▢ ½ cup warm milk (105-115°F)
• ▢ ¼ cup warm water (105-115°F)
• ▢ 1 large egg, room temperature
• ▢ ¼ cup (4 tbsp) unsalted butter, melted and slightly cooled

For the Oreo & Cinnamon Filling:

• ▢ ¼ cup (4 tbsp) unsalted butter, softened
• ▢ ½ cup packed light brown sugar
• ▢ ¼ cup granulated sugar
• ▢ 1 ½ tablespoons ground cinnamon
• ▢ 10-15 Oreo cookies (standard size)

For the Cream Cheese Glaze:

• ▢ 4 oz cream cheese, softened
• ▢ 2 tbsp unsalted butter, softened
• ▢ 1 – 1 ½ cups powdered sugar, sifted
• ▢ ½ – 1 teaspoon vanilla extract
• ▢ 1-2 tablespoons milk or heavy cream (as needed for consistency)

Garnish (Optional):

• ▢ Crushed Oreo cookies

Step-by-Step Instructions

1. Make the Dough & First Rise:

• In a large bowl (or the bowl of a stand mixer), combine about 1 cup of the flour, sugar, instant yeast, and salt. Whisk to combine.
• Add the warm milk, warm water, room temperature egg, and melted butter. Mix with a spoon or the mixer on low speed until a soft, shaggy dough begins to form.
• Gradually add the remaining flour, about ½ cup at a time, mixing until the dough pulls away from the sides of the bowl.
• Knead: Turn the dough out onto a lightly floured surface and knead for 5-7 minutes until smooth and elastic. (Alternatively, use the dough hook attachment on your stand mixer and knead on medium-low speed for 5-7 minutes).
• Place the dough in a lightly oiled bowl, turning once to grease the top. Cover the bowl with plastic wrap or a clean kitchen towel.
• Let the dough rise in a warm, draft-free place for ¹ 1 hour, or until doubled in size.  

2. Roll Dough & Add Filling with Oreos:

• Gently punch down the risen dough. Turn it out onto a lightly floured surface.
• Roll the dough into a rectangle approximately 12×9 inches (or slightly larger if you have more Oreos).
• Spread the ¼ cup of softened butter evenly over the surface of the dough, leaving a small ½-inch border along one of the long edges.
• In a small bowl, combine the brown sugar, granulated sugar, and ground cinnamon. Sprinkle this mixture evenly over the buttered dough.
• Place the whole Oreo cookies in a single row along one of the long edges of the dough, about 1 inch from the edge, and about 1 inch apart from each other.

3. Roll into a Log and Slice:

• Starting from the long edge with the Oreos, tightly roll the dough up into a log, encasing the Oreos and cinnamon-sugar filling.
• Pinch the seam (the ½-inch border you left plain) firmly to seal the log.
• Using a sharp serrated knife or unflavored dental floss, carefully slice the log into 1.5-inch thick rolls. You should get about 9-12 rolls.

4. Second Rise (Proof):

• Lightly grease a 9×13-inch baking dish or two 9-inch round cake pans.
• Place the sliced cinnamon rolls cut-side up into the prepared baking dish(es), leaving a little space between them for expansion.
• Cover the dish(es) loosely with plastic wrap or a kitchen towel. Let the rolls rise in a warm place for another 30 minutes, or until they look puffy.

5. Bake:

• Towards the end of the second rise, preheat your oven to 350°F (175°C).
• Bake the risen rolls for 20-25 minutes, or until they are golden brown and cooked through. The filling should be bubbly.
• Let the rolls cool in the baking dish on a wire rack for about 10-15 minutes before glazing.

6. Make the Cream Cheese Glaze:

• While the rolls are cooling slightly, prepare the glaze. Ensure the cream cheese and butter are properly softened.
• In a medium bowl, using an electric mixer, beat the softened cream cheese and softened butter together until smooth and creamy.
• Gradually beat in the sifted powdered sugar until combined.
• Beat in the vanilla extract.
• If the glaze is too thick, beat in milk or heavy cream, 1 teaspoon at a time, until it reaches a smooth, drizzly, or spreadable consistency, as desired.

7. Glaze and Serve:

• Drizzle or spread the cream cheese glaze generously over the warm (not hot) cinnamon rolls.
• If desired, sprinkle crushed Oreo cookies over the glaze for an extra touch.
• Serve the Oreo-Stuffed Cinnamon Rolls warm and enjoy the decadent deliciousness!

Troubleshooting

• Dough Didn’t Rise: Yeast might be old/expired; liquid (milk/water) too hot (killed yeast) or too cold (didn’t activate); rising environment too cool. Ensure yeast is fresh and liquids are lukewarm.
• Rolls Tough: Over-kneading the dough, or too much flour added. Knead just until smooth/elastic. Add flour gradually.
• Oreos Disintegrated/Lost: This can happen to some extent as they soften. Using whole Oreos helps them maintain some presence.
• Gaps Around Oreos: Dough wasn’t rolled tightly enough around the Oreo row.
• Filling Leaked Excessively: Seam not pinched well, or rolls cut unevenly allowing filling to escape easily.
• Glaze Too Thin/Thick: Adjust with more powdered sugar (to thicken) or more milk/cream (to thin) very gradually.

Tips and Variations

• Yeast Proofing: If using active dry yeast (not instant), proof it in the warm water with a pinch of sugar for 5-10 minutes until foamy before adding to other ingredients.
• Proper Kneading: Develops gluten for structure but don’t overdo it. Dough should be smooth and elastic.
• Warm Rise: A slightly warm (not hot) spot helps dough rise effectively.
• Cutting Rolls: Unflavored dental floss slid under the log and crossed over on top makes very clean cuts without squishing the rolls.
• Oreo Flavors: Experiment with Golden Oreos, Mint Oreos, or Peanut Butter Oreos!
• Add Chocolate Chips: Sprinkle mini chocolate chips over the cinnamon-sugar filling along with the Oreos.
• Different Glaze: A simple vanilla powdered sugar glaze or a chocolate glaze would also be delicious.
• Nuts: Add finely chopped pecans or walnuts to the cinnamon-sugar filling.

Serving and Pairing Suggestions

• Serve Warm: Cinnamon rolls are always best enjoyed warm and gooey!
• Breakfast or Brunch Treat: The ultimate indulgent start to a special day or weekend.
• Dessert: Perfect as a rich dessert.
• With Milk or Coffee: Classic pairings.
• A La Mode: A scoop of vanilla ice cream alongside a warm roll is next-level decadence.

Nutritional Information

(Note: Estimated, per roll, assuming 12 rolls. Very indulgent treat.)

• Calories: 400-550+
• Fat: 18-28g+
• Saturated Fat: 10-18g+
• Cholesterol: 50-70mg+
• Sodium: 250-350mg+
• Total Carbohydrates: 55-75g+
• Dietary Fiber: 1-2g+
• Sugars: 30-45g+ (Very sweet)
• Protein: 5-7g+

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Recipe Summary and Q&A

Summary: These Oreo-Stuffed Cinnamon Rolls feature a homemade yeast dough rolled out, spread with butter and cinnamon-sugar, then lined with whole Oreo cookies before being rolled into a log. The log is sliced into individual rolls, allowed a second rise, then baked until golden brown. Warm rolls are topped with a homemade cream cheese glaze and optional crushed Oreos.

Q&A:

• Q: Can I use store-bought pizza dough or crescent roll dough?
  • A: While you could try, the texture and flavor will be significantly different from a classic sweet yeast cinnamon roll dough. This recipe is designed for a traditional enriched yeast dough.
• Q: Do the Oreos get soggy inside?
  • A: They will soften considerably during baking, becoming part of the gooey interior rather than staying crisp like a fresh cookie. This is part of the charm – you get the Oreo flavor and creamy filling melded into the cinnamon roll.
• Q: Can I prepare these the night before and bake in the morning?
  • A: Yes! After placing the sliced rolls in the baking dish (Step 4), cover them tightly with plastic wrap and refrigerate overnight for the second rise (this is a cold proof). In the morning, let them sit at room temperature for about 30-45 minutes while the oven preheats, then bake as directed (they might need a few extra minutes).
• Q: How do I store leftover rolls?
  • A: Store leftover frosted rolls in an airtight container at room temperature for 1-2 days, or refrigerated for up to 4-5 days. Reheat gently in the microwave or oven before serving for best taste and texture.