Cinnamon Bread with Date Filling

1.In a bowl of a stand mixer, pour 1/4 cup warm water. Sprinkle yeast and 1 teaspoon sugar and let this mixture sit until it is foamy, about 5-8 minutes. Add the milk, softened butter, egg, 1/4 cup sugar, 2 teaspoons cinnamon and salt turn the mixer on low and let the ingredients combine.
2.Add 3 cups of flour, one cup at a time while the machine is on low, until the dough gathers into a shaggy mass. If the dough is still too wet, add the rest of the 1 cup of flour until the dough comes together.
3.Continue to knead the dough in the mixer until it is smooth and elastic about 10 minutes. Shape the dough into a ball cover the bowl with plastic wrap and allow it to rise for 1½ hours or until the size is doubled.
4.Meanwhile, in a bowl, pour hot water over the dates so that they are fully submerged. Allow the mixture to sit for 10-15 minutes, or until the dates are soft and mushy. Drain the mixture and process the dates in a food processor into a paste-like consistency. In a small bowl mix brown sugar plus 2 teaspoons cinnamon.
5.Gently deflate the risen dough and using a rolling pin, roll it into a rectangle that is ¼ inch thick. Spread the Medjool dates paste over the dough. Sprinkle brown sugar with cinnamon on top of the dates. Starting on the long edge, roll the dough into a tight log. Press the ends to seal and position the log with the seams side down.
6.Starting 1 inch below the topmost part of the log, slice the log through the middle up to the other end, forming two open flaps. Rotate the flaps so that the cut sides are up. Put one flap over the other and repeat the process until you reach the end of the log. Tuck the ends underneath to seal.
7.Let it rise for another hour. Meanwhile, mix the powdered sugar and heavy cream together and set aside. Preheat the oven to 350F and bake for 20-22 minutes, or until golden. Let the loaf cool slightly. Drizzle with sugar glaze.