Make the dough: Heat milk to about 95°F (35°C)– use microwave or stovetop. Pour the warm milk into the bowl of a stand electric mixer fitted with the dough hook attachment (OR you can use a handheld mixer OR no mixer, but a stand mixer is ideal). With a whisk, manually whisk in the sugar and yeast. Cover with a towel and let sit until the yeast is foamy, about 5-10 minutes. If the yeast does not dissolve and foam, start over with fresh active yeast. On low speed, beat in the softened butter until it is slightly broken up. Next add the eggs, one at a time, and then the salt. The butter won’t really be mixing into the mixture, so don’t be alarmed if it stays in pieces. On low speed, gradually add the flour. Once it is all added, beat on medium speed until a soft dough forms. Increase speed to medium-high and beat until the dough is soft and supple, about 6 minutes longer. *If you do not have a stand-mixer with a hook attachment, knead the dough by hand in this step.
Transfer the dough to a lightly floured surface and knead it with your hands for 1 minute. Form the dough into a ball and transfer it to a lightly greased bowl. Cover the dough loosely with plastic wrap, a paper towel, or aluminum foil and let sit in a warm place until doubled in size, about 1 to 2 hours.
Line a large baking sheet with parchment paper. Lightly flour the parchment paper. Place the dough on top and, with floured hands, pat down to roughly form a 10×20-inch rectangle. Make sure the dough is smooth and evenly thick.
For the filling: Spread the softened butter all over the dough. In a small bowl, toss the cinnamon and sugar together until combined and then sprinkle evenly over the dough. Tightly roll up the dough to form a 20-inch long log. Cut into 20 1-inch rolls, only slicing 3/4 of the way through so they are still connected at the bottom. Use kitchen shears if you need to.
Shape the wreath: Turn one of the end cinnamon rolls on its side. Turn the next one so that it slightly overlaps the first. Repeat with each roll, forming into a circle and overlapping each. Again, kitchen shears help to cut any dough as you’re shaping.
Place a ramekin in the middle of the wreath. This will help it hold its shape.
Cover the wreath loosely with plastic wrap and slide a baking sheet underneath the whole thing. Use a large one with no edges so it can slide under easily. Allow to rise again in a warm environment until puffy, about 45 minutes – 1 hour.
Preheat the oven to 350°F (177°C). Bake for about 25 minutes, until the rolls are golden brown. Remove from the oven and allow to cool for 10 minutes before topping with icing.
Make the icing: Whisk all of the icing ingredients together in a medium bowl. Drizzle over wreath.