In a small bowl, combine warm water (110°F or 43°C) and active dry yeast. Let sit for about 5 minutes until foamy.

In a large mixing bowl, combine pumpkin puree, whole milk, melted unsalted butter, granulated sugar, salt, egg, and chai spice mix. Whisk until smooth.

Gently stir the yeast mixture into the pumpkin mixture until fully incorporated.

Gradually add all-purpose flour to the wet ingredients, one cup at a time, until a soft dough forms.

Transfer the dough onto a floured surface and knead for about 8 minutes until smooth and elastic.

Cover the bowl with a towel and let the dough rise for 1 to 1.5 hours until doubled in size.

Prepare the filling by mixing softened butter, brown sugar, cinnamon, and additional chai spice in a bowl.

Once the dough has risen, roll it out into a rectangle, approximately 16x12 inches, and spread the filling evenly.

Starting from one long edge, roll the dough tightly into a log and slice into 12 equal pieces.

Cover the rolls and let them rise for an additional 30 minutes.

Preheat the oven to 375°F (190°C) and bake for 20 to 25 minutes until golden brown.

Prepare the icing by mixing powdered sugar, cream cheese, melted butter, milk, and vanilla extract until smooth.

Let the rolls cool for 10 minutes before drizzling with icing.