Bloom the Yeast: Combine 1 cup of warmed whole milk, 2 tablespoons of granulated sugar, and 2 teaspoons of active dry yeast in a bowl. Stir and let sit for 10 minutes until frothy.

Prepare the Dough: Mix 4 cups of flour, 1 teaspoon of salt, 1 teaspoon of ground cinnamon, and chai spices in a mixer. Add eggs, 2 teaspoons of vanilla, and bloomed yeast mixture. Mix in 1/2 cup softened butter until smooth.

Proof the Dough: Place dough in a greased bowl, cover, and let rise in a warm area for 1 to 1.5 hours until doubled.

Make Caramel Sauce: Heat 1 cup of heavy cream, steep 2 chai tea bags for 10 minutes, then combine with 1/2 cup butter, 1 cup brown sugar, and 2 tablespoons honey until smooth. Spread in a baking dish.

Make Filling: Combine 1/2 cup softened butter with 3/4 cup brown sugar and chai spices in a bowl until creamy.

Roll and Cut Dough: Punch down risen dough, roll out to a rectangle, spread the filling, roll tightly, and cut into 12 rolls.

Second Proof: Place rolls over caramel sauce, pour 1/2 cup of heavy cream, cover, and let proof for another hour.

Bake: Preheat oven to 350°F and bake rolls for 29-32 minutes until golden brown.

Prepare Frosting: Beat 8 ounces of cream cheese and 1/4 cup butter until smooth, then mix in 2 cups powdered sugar.

Frost and Serve: Let baked rolls cool for 10 minutes, drizzle with frosting, and enjoy warm.