Warm 1¼ cups milk, either on the stove top or in the microwave for about 1 minute 30 seconds, until it's like a warm bath when you put your finger in the milk.
Sprinkle the one active dry yeast packet (2¼ tsp) on the milk and let it sit for about 5 minutes, until it becomes frothy.
Whisk in ½ cup granulated sugar, 6 Tbsp softened butter, 2 large eggs, 1 Tbsp vanilla extract, and 1 tsp fine sea salt.
Gradually add 4½ to 5 cups of flour, one cup at a time. Using a wooden spoon, mix the dough after each flour addition until there is no longer dry flour visible. Mix until the dough is very thick slightly sticky.
Flour a clean work surface and knead the dough by hand for about 6 to 8 minutes, until the dough is smooth and springs back to it's original shape when you indent it with your finger. Shape the dough into a ball.
Spray the dough ball and a bowl with cooking spray or lightly brush them with vegetable oil. Put the dough ball in the greased bowl and cover with plastic wrap. Let it rest and rise in a warm place (like an empty oven with the light turned on) for about 2 hours, until it doubles in size.
Using a needle and thread, carefully thread the fresh cranberries lengthwise onto the string. Don't cut the string yet, so you may need to add or remove berries to match the length of the dough. You'll probably need about ⅓ to ½ cup fresh cranberries.
As the dough nears the end of its rising period, prepare the filling. Cream the remaining 10 Tbsp of softened butter with 2 Tbsp ground cinnamon, ¾ cup packed brown sugar with a whisk or mixer. It will form a thick and delicious paste.
Sprinkle some flour on a clean work surface and roll out the dough into a large rectangle, about 14 inches by 24 inches.
Evenly spread out the filling onto the dough rectangle, getting it all the way to the edges.
Gently roll the dough starting at one of the long edges, to form a giant swirly log or burrito.
Using a sharp knife, make two cuts down the entire length of the cinnamon roll log, to separate it into three very long strips. Using your knife or your fingers, gently roll the strips of dough so the cut-side (the cinnamon filling) faces up.
Measure your string of cranberries along the length of the middle strand of dough. Add or remove cranberries from the thread as needed, in order to make it the same length as the dough. Leave a bit of extra string above the top of the dough and tape the string to your work surface, to prevent it from moving.
Gently press the three strands together at the top and braid them together, keeping the string of cranberries with the middle strand of dough as you braid it. The braid shouldn't be so loose that you see gaps between the strands, but it shouldn't be so tight that you pull and risk tearing the dough. #goldilocks
Transfer the dough to a sheet pan (greased with cooking spray, lined with parchment paper, or on a silpat). Bring the two ends of the dough braid together, to form a circle.
Remove the string from the cranberries by removing the tape from the work surface and tugging the string through all the cranberries. You may need to cut the string at a couple different points along the cranberry line to be able to gently pull it out without disturbing the dough.
Cover the dough wreath loosely in plastic wrap and let it rise in a warm place for about 1 hour, until the dough doubles in size.
Bake at 350°F for about 20 to 25 minutes, until it is golden brown.
Take the cinnamon roll wreath out of the oven and while it cools, prepare the icing. In a small bowl, use a whisk or a fork to combine 1 cup powdered sugar, 2 Tbsp lemon juice and 1 Tbsp milk. Add another Tbsp milk, if needed, until it is a drizzle-able consistency.
Drizzle on the icing. Let it cool for 10 minutes, then enjoy!