First things first, gather all your ingredients on the counter. This makes things smoother. Besides the fridge, the kitchen should be your favorite space. Make sure your cream cheese is softened to mix easily with the other filling ingredients.
Grab a zip-top bag and toss in the Oreos. Seal the bag and let out any frustrations—using a rolling pin, crush those cookies until they are finely ground. You want a fine crumb texture with no large chunks. This step adds sweetness and crunch.
In a mixing bowl, combine the softened cream cheese, crushed Oreos, chocolate chips, and vanilla extract. Use a spatula or mixer to blend everything until it’s smooth and creamy. Don’t worry! You won’t only be licking the spoon later; this filling is downright irresistible.
Open the can of Pillsbury™ Grands!™ Cinnamon Rolls. Take each roll and gently flatten it with your hands. Make sure to keep the seal intact. You are creating a little pocket for the filling that will soon rock your world.
Spoon a generous dollop of the Oreo filling into the center of each flattened cinnamon roll. Fold the dough over the filling to close it. You want it to be well sealed to prevent the filling from oozing out while baking. With a gentle pinch and movement, give them a good shape.
Preheat your oven to 350°F (or 175°C). Place the filled rolls in a greased baking dish. Cover them with a kitchen towel and allow them to rise for about 20 minutes. It lets them fluff up! Bake for about 15-20 minutes until golden brown. The aroma wafts through the kitchen, and if you can resist, you have a stronger will than I do.
Let the rolls cool slightly before drizzling the included frosting on top. If you’re feeling adventurous, you can make a simple icing with powdered sugar and a splash of milk. Then it’s time for the ultimate taste test. Grab your fork and dive in!