Preheat the Oven: Preheat your oven to 375°F (190°C). Line a baking sheet with parchment paper to prevent sticking.
Prepare the Cinnamon Sugar: In a small bowl, mix together the brown sugar and ground cinnamon. Set aside.
Roll Out the Dough: Unroll the crescent roll dough on a flat surface. Press the seams together to create a large rectangle.
Add the Filling: Brush the melted butter evenly over the dough. Sprinkle the cinnamon-sugar mixture over the buttery surface, followed by the chopped cranberries. If using, add the orange zest for a citrusy punch.
Form the Rolls: Starting from one long edge, gently roll the dough into a tight log. Once rolled, slice the log into 1-inch pieces to create bite-sized rolls.
Arrange and Bake: Place the sliced rolls on the prepared baking sheet, leaving space between each bite. Bake in the preheated oven for 15-20 minutes or until golden brown and flaky.
Prepare the Icing: While the rolls are baking, whisk together the powdered sugar, milk, and vanilla extract in a small bowl until smooth. Adjust the thickness of the icing by adding a bit more milk or powdered sugar if needed.
Finish and Serve: Once the rolls are done, remove from the oven and allow them to cool slightly. Drizzle the icing over the warm cinnamon roll bites. Serve immediately and enjoy the warm, flaky goodness!