📝 Instructions
Step 1: Prepare the Dough
- Activate Yeast: In a large bowl or the bowl of a stand mixer, warm the milk for 30-40 seconds until it is lukewarm.23 Stir in the yeast and granulated sugar. Cover and let it sit for 5-10 minutes until frothy. This is called proofing and shows your yeast is active.
- Mix Wet Ingredients: Whisk in the melted butter, egg, and vanilla extract until well combined.
- Add Dry Ingredients: Mix in the salt. Gradually add the flour, 1 cup at a time, mixing until a soft, slightly sticky dough forms.
- Knead: Turn the dough out onto a lightly floured surface and knead for 5-7 minutes until the dough is smooth and elastic. If using a stand mixer with a dough hook, knead on medium-low speed for 5-6 minutes.
- First Rise: Place the dough in a lightly greased bowl, turning to coat. Cover with plastic wrap or a clean kitchen towel. Let the dough rise in a warm place for 1 to 1.5 hours, or until it has doubled in size.24
Step 2: Make the Filling and Shape the Rolls
- Prepare Filling: While the dough rises, prepare the filling. In a medium bowl, combine the softened butter, brown sugar, cinnamon, crushed Oreos, and black cocoa powder (if using).25 Mix until well combined and spreadable. Set aside.
- Roll Out Dough: Punch down the risen dough to release the air. On a lightly floured surface, roll the dough into a large rectangle, approximately 26$14 \times 18$ inches and about 27$1/4$ inch thick.28
- Spread Filling: Evenly spread the Oreo cinnamon filling over the entire surface of the dough, leaving about a $1/2$-inch border on one of the long edges.
- Roll and Cut: Starting from the opposite long edge, tightly roll the dough into a log. Use a sharp, non-serrated knife or unflavored dental floss to cut the log into 12 equal pieces (about 29$1.5$ inches thick each).30
- Second Rise: Arrange the rolls, cut-side down, in a lightly greased 31$9 \times 13$-inch baking dish.32 Cover the pan with a clean kitchen towel and let them rise again in a warm spot for 45-60 minutes, or until they look puffy.
Step 3: Bake and Frost
- Preheat & Bake: Preheat your oven to 33$350^\circ\text{F}$ (34$175^\circ\text{C}$).35 If desired, you can gently pour about 36$1/4$ cup of heavy cream over the rolls before baking (this makes them extra gooey!). Bake for 22-28 minutes, or until the tops are lightly golden brown.37 Avoid over-baking!
- Make Frosting: While the rolls bake, prepare the frosting. In a medium bowl, beat the softened cream cheese and butter until smooth. Gradually beat in the sifted powdered sugar and vanilla extract. Add milk or heavy cream, 1 tablespoon at a time, until the frosting reaches a smooth, spreadable consistency.
- Frost and Serve: Let the rolls cool in the pan for about 5-10 minutes.38 Spread the cream cheese frosting generously over the slightly warm rolls. Sprinkle the top with the reserved crushed Oreos. Serve immediately and enjoy the cookies-and-cream goodness!
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