Preheat your oven to 375°F (190°C) and line a baking sheet with parchment paper.
In a mixing bowl, beat the softened cream cheese with sugar and vanilla until smooth and creamy, about 2-3 minutes.
Unroll the crescent dough onto a lightly floured surface and gently press seams together to form a solid sheet. Roll it out slightly to even the thickness, about 1/8 inch.
Spread the cream cheese mixture evenly over the dough, leaving a small border around the edges.
Mix cinnamon and sugar in a small bowl, then sprinkle it evenly over the cream cheese layer to create a cinnamon swirl effect.
Starting from one side, carefully roll the dough into a tight log, similar to a jelly roll, ensuring the filling stays inside.
Gently shape the rolled dough into a circular wreath on the prepared baking sheet, joining the ends together and pinching to seal.
Brush the top of the wreath with the beaten egg for a shiny, golden finish.
Bake in the preheated oven until the wreath is golden brown and puffed, about 25-30 minutes.
Remove from oven and let it cool slightly. Mix milk with a little powdered sugar if desired to create a glaze; drizzle over the warm wreath for added sweetness and shine.
Slice and serve while still warm to enjoy the soft, creamy filling and crisp, flaky exterior.
