Oreo Stuffed Cinnamon Rolls

Pillowy homemade dough envelops crushed chocolate sandwich cookies and warm cinnamon sugar in these indulgent rolls that create the ultimate breakfast-dessert hybrid. Cream cheese icing melts into each warm spiral, adding another layer of sweetness to this creative twist on classic cinnamon rolls.

I stumbled upon this combination when experimenting with leftover cookies during a rainy weekend baking session. The first batch disappeared within minutes of coming out of the oven, with my husband declaring them "dangerously good." Something magical happens when the cookie pieces melt slightly into the cinnamon-sugar mixture, creating pockets of chocolate goodness throughout each roll. They've since become our special occasion breakfast tradition.

Sweet Components

• Active dry yeast: Creates the perfect rise for soft, fluffy dough that stays tender
• Warm milk: Activates yeast while adding richness to the dough structure
• All-purpose flour: Provides structure while maintaining tenderness in the final product
• Unsalted butter: Adds richness to both dough and filling for perfect flavor
• Crushed Oreo cookies: Create chocolatey pockets throughout each roll
• Ground cinnamon: Provides warming spice that perfectly complements chocolate
• Cream cheese: Creates tangy balance in the sweet icing
• Vanilla extract: Enhances all flavors with its aromatic depth

My favorite part of making these rolls is watching people's faces when they take their first bite - there's always that moment of surprise when they encounter the chocolate cookie pieces nestled within the familiar cinnamon roll. The contrasting textures between the soft dough, slightly melted cookies, and creamy icing create something truly extraordinary.

Baking Method

Activate your yeast:

Combine warm milk with yeast and sugar, allowing mixture to become frothy and active.

Create dough foundation:

Mix remaining sugar with eggs, butter and salt before incorporating activated yeast mixture.

Develop proper structure:

Add flour gradually while kneading until smooth, elastic dough forms with perfect texture.

Allow first rise:

Place dough in warm location until doubled in size, developing both flavor and structure.

Prepare filling components:

Combine butter, sugar and cinnamon for traditional base while crushing cookies separately.

Create perfect canvas:

Roll dough into large rectangle with even thickness for consistent results throughout.

Add flavor layers:

Spread cinnamon mixture evenly before sprinkling crushed cookies across entire surface.

Form perfect spirals:

Roll dough tightly from long edge, pinching seam to seal before cutting into portions.

Complete final rise:

Allow cut rolls to rise again, creating even more pillowy texture before baking.

Transform with heat:

Bake until golden brown and fragrant, with filling bubbling slightly at edges.

Create creamy finish:

Beat together icing ingredients until smooth before drizzling over warm rolls.

Enjoy at peak perfection:

Serve while still slightly warm for the ultimate melty, gooey experience.

I've found these cinnamon rolls bring people together in a unique way. Last Christmas morning, my usually quiet brother-in-law became animated describing exactly what made them so delicious. There's something about the combination of familiar flavors in a surprising new form that sparks joy and conversation. They've become something of a signature recipe in our family, requested for special occasions and weekend visits.

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Serving Suggestions

• Pair with fresh berries to balance the richness with bright, natural acidity that complements both chocolate and cinnamon.
• Serve alongside strong coffee or cold milk, both of which provide perfect counterpoints to the sweet, rich rolls.
• Present on a tiered serving plate for brunch gatherings, creating an impressive centerpiece that invites sharing.

Creative Variations

• Substitute mint-filled chocolate sandwich cookies for a refreshing twist that adds complexity to the flavor profile.
• Add orange zest to the dough for bright citrus notes that beautifully complement both chocolate and cinnamon.
• Incorporate chopped nuts like pecans or walnuts into the filling for additional texture and nutty depth.

Storage Solutions

• Store completely cooled rolls in an airtight container at room temperature for up to two days, maintaining optimal texture.
• Refrigerate rolls for longer storage up to five days, bringing to room temperature or warming briefly before serving.
• Freeze unfrosted rolls tightly wrapped for up to two months, thawing completely before warming and adding fresh icing.

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The magic of these cinnamon rolls lies in how they transform familiar flavors into something unexpectedly delightful. They remind me that creativity in baking often comes from combining beloved classics in new ways. While they require some time and patience, most of that is hands-off rising time, making them accessible even to those newer to bread baking. The moment when the kitchen fills with the aroma of cinnamon, butter, and chocolate is worth every minute of preparation.

Frequently Asked Questions

→ Can I prepare these cinnamon rolls the night before?

Yes, you can prepare them through the second rise, then cover and refrigerate overnight. Let them come to room temperature for about 30 minutes before baking.

→ What can I substitute for cream cheese in the icing?

You can make a simple glaze with powdered sugar, vanilla, and milk if you don't have cream cheese available.

→ Can I freeze these cinnamon rolls?

Yes, you can freeze them either before or after baking. If freezing before, freeze after shaping but before the second rise. If freezing after baking, freeze without icing and add fresh icing when serving.

→ How do I know when the dough has risen enough?

The dough should roughly double in size. Press it gently with your finger - if the indentation remains, it's ready.

→ Can I use different flavors of Oreos?

Absolutely! Try mint, golden, or seasonal Oreo varieties for different flavor combinations.