Prepare the Crust:
Mix graham cracker crumbs, brown sugar, and cinnamon in a bowl. Stir in melted butter until combined. Press into the bottom of a 9-inch springform pan. Chill in the refrigerator for 15 minutes.

Make the Cinnamon Filling:
Mix brown sugar, cinnamon, flour, and melted butter until smooth. Set aside.

Prepare the Cheesecake Filling:
In a large bowl, beat cream cheese and sugar until smooth. Add eggs one at a time, mixing well. Stir in sour cream and vanilla until fully combined.

Assemble:
Pour ⅓ of the cheesecake filling over the crust. Drizzle ⅓ of the cinnamon filling over the batter. Swirl with a knife. Repeat layers two more times, ending with a swirl.

Bake:
Preheat oven to 325°F (163°C). Place the springform pan in a larger baking dish. Fill the outer dish with hot water (water bath) halfway up the springform pan. Bake for 55-65 minutes, until the center is set but slightly jiggly. Turn off the oven, crack the door, and let the cheesecake cool inside for 1 hour. Remove and chill for 4 hours or overnight.

Make the Glaze:
Whisk powdered sugar, milk, and vanilla until smooth. Drizzle over chilled cheesecake before serving.