Step 1: Prepare the Dough

In a large bowl, combine 1 cup warm milk and 2 1/4 teaspoons active dry yeast. Let it sit for about 5 minutes until the yeast becomes bubbly and foamy.

Add 1/4 cup sugar, 1/2 teaspoon salt, and 1/2 cup melted butter to the yeast mixture. Stir until the sugar dissolves.

Add 2 large eggs and 3 1/2 cups flour (one cup at a time), mixing well after each addition.

Knead the dough for 5-7 minutes until smooth and elastic. If the dough is too sticky, add more flour, one tablespoon at a time.

Once the dough is smooth, place it in a greased bowl and cover it with a clean towel. Let it rise in a warm place for 1 to 1 1/2 hours or until it doubles in size.

Step 2: Prepare the Filling

While the dough is rising, make the filling. In a medium bowl, mix 1/2 cup softened butter, 1 cup brown sugar, and 2 tablespoons ground cinnamon until smooth.

Crush 1 cup of Oreos into small pieces. You can do this in a food processor or by placing the cookies in a zip-top bag and smashing them with a rolling pin. Set aside.

Step 3: Roll Out the Dough

Once the dough has risen, punch it down to release any air bubbles. Place the dough on a floured surface and roll it out into a large rectangle, about 1/4 inch thick.

Spread the cinnamon-sugar butter mixture evenly over the dough, leaving a small border around the edges.

Sprinkle the crushed Oreos evenly on top of the cinnamon-sugar mixture.

Step 4: Roll and Slice the Dough

Starting from one of the longer sides of the dough, tightly roll it up into a log. Be careful not to roll it too tightly to avoid squeezing out the filling.

Use a sharp knife to slice the rolled dough into 12 equal pieces.

Place the rolls into a greased 9×13-inch baking dish, leaving a little space between each roll.

Cover the dish with a clean towel or plastic wrap and let the rolls rise for 30-45 minutes until they puff up.

Step 5: Bake the Rolls

Preheat the oven to 350°F (175°C).

Once the rolls have risen, place them in the preheated oven and bake for 25-30 minutes, or until golden brown on top.

You’ll know the rolls are done when the edges are lightly browned, and a toothpick inserted in the center comes out clean.

Step 6: Make the Cream Cheese Frosting

While the rolls are baking, prepare the frosting. In a medium bowl, beat 8 oz softened cream cheese and 1/4 cup softened butter together until smooth.

Add 1 1/2 cups powdered sugar and 1 teaspoon vanilla extract and beat until the frosting is creamy and fluffy.

Once the rolls are done baking, spread the cream cheese frosting over the warm rolls, letting it melt into the crevices.

Garnish with 1/4 cup crushed Oreos for an extra touch of crunch.