Heat the milk in a saucepan over medium-low heat until just warm, around 105-110 degrees F. Stir in 1 tablespoon of the sugar. Sprinkle the yeast overtop and let sit until foamy, about 5 minutes. Once foamy, whisk in the eggs until smooth.
Place the flour and salt in the bowl of your electric stand mixer (I used the paddle attachment). Slowly add the milk mixture and mix on low speed until combined. Add the butter 1 piece at a time, beating until combined. Mix on medium-high speed for 5 minutes to knead the dough, it should be silky and smooth. Remove the dough and place it in an oiled bowl, then cover with plastic wrap. Let sit and double in size for 1 to 2 hours.
While the dough is rising, make part of the filling. Add the cranberries, orange juice and granulated sugar to a saucepan over medium heat. Stir until the sugar dissolves then bring the mixture to a bubble – cook for 5 to 6 minutes as the cranberries begin to break down and the mixture thickens. Remove it from the heat to cool completely. You can even do this part ahead of time!
Right before the dough is ready, make the cranberry caramel. Add the butter to a saucepan over medium heat. Once melted, stir in the sugar, cream, honey, cranberries and salt. Bring to a boil then reduce to a simmer and cook for 3 to 4 minutes until glossy and smooth – and the cranberries begin to burst. Remove from heat and stir in the vanilla extract. Let sit to thicken and cool slightly.
Take the dough and roll it out on a floured surface into a large rectangle, about 18 x 12 inches or so. Brush the melted butter all over the dough. Combine the sugar and cinnamon and sprinkle it over top. Add on the cranberry filling and gently spread it around. Sprinkle on the white baking morsels. Tightly roll the dough up from one of the long ends into a long log. Slice the ends off and discard them, then slice the log into 24 equal slices, about ½ inch thick. Place the rounds in the muffin pan, on top of the cranberry caramel. Brush with melted butter and cover with plastic wrap. Let rise in a warm place for 30 to 45 minutes.
Preheat the oven to 350 degrees F. Bake the buns, uncovered, for about 30 to 35 minutes. Remove from the oven and use a spoon to invert all of the muffins onto a serving tray or platter. Drizzle with the remaining cranberry caramel. Serve hot!