Prepare dough by first warming the milk and chai tea on the stove in a small saucepan on low heat, stirring constantly. Remove from heat when warm (do not allow to boil!). Add all ingredients into a standard bread machine and place on “dough” setting.
When dough is ready, approximately 1.5 hours later, remove from pan onto a lightly floured surface. Knead once or twice and roll out to ½ – ¾” thick circle. Using a knife, spread butter evenly over the dough. Top with sugar, spices and apples. Gently roll the dough in, gathering the filling so it’s fairly tight in the roll.
Preheat oven to 175 degrees. Using a sharp knife, slice the roll into 1 ½” thick wedges, placing in a greased baking pan (any size pan is fine).
Cover pan of rolls with a lightweight towel and place in the warm oven for about another 30-40 minutes, or until rolls have nearly doubled in size. Remove from the oven, leaving the towel on and heat oven up to 375 degrees. When oven has preheated, remove towel and place pan in oven. Bake for approximately 15 minutes or until rolls are lightly browned.
While rolls are baking, prepare glaze by adding the butter, cream, vanilla and whiskey to a mixing bowl. With whisk attachment, beat on low until mixed. Slowly add sifted powdered sugar. Watch the consistency and beat until it’s creamed. You may need to add a touch more cream if it’s too thick, or more sugar if it’s too thin (depends on the weather and how exact your measurements are).
When rolls are lightly browned, remove from oven. Allow to cool for about 10 minutes and then drizzle glaze over the top. Serve warm and store any leftovers in an airtight container for up to 2 days.