Step 1: Preheat Your Oven

Start by preheating your oven to 350°F (175°C). This ensures even baking and that the rolls rise properly.

Step 2: Prepare Your Baking Dish

Lightly grease a round cake pan, an 8×8-inch baking dish, or a muffin tin if you want individual rolls with crisp edges. You can also line with parchment for easy cleanup.

Step 3: Crush the Oreos

Place 8–10 Oreo cookies in a resealable bag and gently crush them with a rolling pin. You want medium chunks—avoid turning them into dust. Chunks give better texture and chocolate pockets.

Step 4: Make the Oreo Filling

In a bowl, mix the crushed Oreos with 2 tablespoons melted butter and 1/2 teaspoon vanilla extract. This step adds richness and moisture, helping the filling blend seamlessly with the dough.

Step 5: Open and Unroll the Cinnamon Rolls

Gently separate the rolls and unroll each one into a flat strip. If your dough resists, let it sit at room temperature for a few minutes.

Step 6: Stuff and Re-Roll

Spread 1–2 teaspoons of the Oreo filling across each strip. Roll the dough back into spirals, gently pressing to seal the cookies inside.

Step 7: Arrange and Bake

Place the rolls into your prepared pan. Bake for 18–22 minutes, or until golden brown and baked through. Avoid overbaking; the goal is a gooey center.

Step 8: Ice While Warm

Remove from the oven and immediately spread the cream cheese icing on top of each roll. The warmth helps melt the icing into all the nooks and crannies.

Step 9: Garnish with Extra Crushed Oreos

For the perfect finish, sprinkle extra crushed Oreos over the top. This adds a decorative touch and an extra punch of cookie flavor.

Step 10: Serve and Enjoy!

Serve warm for the ultimate indulgence. Pair with a glass of cold milk, a cup of coffee, or a scoop of vanilla ice cream for dessert.