Prepare the Cheesecake Base: Preheat the oven to 325°F (160°C). In a medium bowl, beat the softened cream cheese until smooth. Add the granulated sugar and vanilla extract, mixing until well combined.
Incorporate Eggs: Add the eggs one at a time, mixing well after each addition. Lastly, stir in the flour until just combined. Set aside.
Make the Cinnamon Roll Filling: In another bowl, mix together the brown sugar, ground cinnamon, and melted butter. Gradually add the flour until the mixture resembles a crumble.
Layer the Cheesecake: Pour half of the cheesecake batter into a greased 9-inch springform pan. Spread half of the cinnamon roll filling evenly over it. Pour the remaining cheesecake batter on top and finish by sprinkling the remaining cinnamon roll filling over the top. Use a knife to swirl slightly for a marbled effect.
Bake: Place the springform pan in the center of the preheated oven and bake for about 50-60 minutes, or until the cheesecake is set but slightly jiggly in the middle. Turn off the oven and leave the cheesecake inside for an additional hour for even cooling.
Cool and Refrigerate: Remove the cheesecake from the oven and allow it to cool at room temperature for 30 minutes before transferring it to the fridge. Chill for at least 4 hours, preferably overnight.
Prepare the Topping: In a small bowl, whisk together powdered sugar, milk, and vanilla extract until smooth. Adjust the milk to achieve your desired consistency (thicker or thinner).
Serve: Once chilled, drizzle the glaze over the cheesecake. Carefully remove the sides of the springform pan.
Notes
Slice the cheesecake into wedges and serve on individual dessert plates. Garnish with a sprinkle of cinnamon or a dollop of whipped cream for an extra touch.