Preheat oven to 325 °F (163 °C). Grease a 9‑inch springform pan.

In a bowl, mix graham crumbs, melted butter, granulated sugar, and cinnamon until it resembles wet sand. Press firmly into the pan’s bottom and bake for 8–10 minutes. Let it cool.

In a large bowl, beat the softened cream cheese and sugar until smooth. Add eggs one at a time, then stir in vanilla.

Mix brown sugar and cinnamon for the swirl.

Pour half the filling over the crust. Sprinkle half the swirl mixture over it. Pour remaining filling, then the remainder of the swirl mixture. Gently swirl with a toothpick or skewer.

Bake for 50–55 minutes (or 55–65 depending on your oven) until the center is set but still jiggles slightly. Turn off oven, crack door open, and let it cool inside for about 1 hour.

Refrigerate for at least 4 hours or overnight before glazing.

Whisk together powdered sugar, milk, and vanilla; drizzle over the chilled cheesecake.