In the bowl of an electric stand mixer, combine yeast and warm water. Let it sit for a couple minutes or until it starts to bubble. Mix on low and add the milk, sugar, butter, salt, cinnamon, and eggs. Add two cups of the flour, one cup at a time. Beat for 2 minutes. Add remaining flour 1/2 cup at a time until dough is soft and workable and comes away from the side. You may not need it all depending on the time of year and level of humidity.
Oil a large bowl and set aside. Turn the dough out on a lightly floured work surface and knead for 5 to 10 minutes or until smooth. Place in the oiled bowl, turning once to oil both sides. Cover with plastic wrap and allow to rise in a warm place until doubled about 90 minutes. Prepare filling while dough rises.
In a medium-sized saucepan combine filling ingredients. Cook until thick. Remove from the stove. If filling gets too thick stir in additional water.
When the dough has doubled in size, lightly flour a working surface and roll out into a 9x30 rectangle. Spread filling onto the dough within one inch of the edges. Roll the dough tightly starting from the long edge, pinching the ends to seal. With a sharp knife, cut the roll in half lengthwise. Carefully turn the halves so the cut sides face up and then loosely twist the halves around each other, keeping cut sides up. I started from the middle and worked up and then down.
Line a baking sheet with parchment or non-stick baking mat. Carefully transfer the rope to the baking sheet and shape into a circle. Tuck the ends together. Cover loosely with plastic wrap and then a kitchen towel. Let rise in a warm place until puffy, about 45 minutes.
Preheat oven to 350° F. Bake the wreath until lightly browned, 20-25 minutes. Cool completely on a cooling rack.
Drizzle glaze over the wreath once cooled or before serving if bread was made ahead of time.
Store in an airtight container at room temperature.
Dough recipe adapted from "Holiday Breakfast Wreath" by kitchn.com. Prep time includes non-active rising time.