Heat the milk to 110 degrees F and stir in yeast and sugar. If using active dry yeast, allow to sit for 15 minutes. If using instant yeast, simply move on to the next step.

Mix the eggs and vanilla into the milk yeast mixture.

Combine flour and salt together in the bowl of a stand mixer fitted with a dough hook.

Pour the wet ingredients into the flour and mix on low-medium speed for about 3 minutes, or until it forms a ball around the hook.

Add in one piece of butter at a time, allowing it to fully incorporate before adding the next.

Once all of the butter is incorporated, turn the mixer up to medium-high speed and mix for 8-12 minutes. To check if the dough is ready, tear off a small piece and carefully spread it out to see if you can see the light through it without it tearing. If it tears, mix for another minute and check again.

Once the dough is ready, transfer it to a lightly greased bowl, cover, and allow to proof overnight in the fridge. Alternatively, you can let the dough rise in a warm place for about 1 hour or until doubled in size.

Add the cranberries, sugar, orange zest, orange juice, cinnamon, and salt to a medium saucepan. 

Heat over medium heat for 10-12 minutes stirring often until the cranberries start to break down. 

Reduce heat to low, and cook for another 8-10 minutes, stirring frequently until it has thickened. 

Remove from heat and use an immersion blender (or transfer to a blender) and blend until smooth.

Pour into a glass jar to cool completely, then chill in the fridge until ready to use. 

On a lightly floured surface, roll the brioche dough out into a rough rectangle about ¼'' in thickness.

Spread about 225g (about 1 cup) of the jam out evenly over the dough.

Using a ruler (or you can eyeball it), measure out 9 1 ½-inch rolls by scoring lines with a knife.

Use dental floss to cut each roll by placing the floss under the dough, wrapping around, and pulling to cut through. 

Place each roll in a baking dish (measuring at least 10.5"x7.5"), cover, and allow to rise at room temperature for 30 minutes. 

Towards the end of the proof time, preheat the oven to 350 degrees F.

Bake the cranberry orange cinnamon rolls for 22-25 minutes until barely golden.

While the cinnamon rolls are baking, make the icing. In a medium bowl, add the cream cheese, melted butter, and sifted powdered sugar. 

Whisk vigorously until smooth and the mixture flows off of the whisk. 

Spread all over the warm cranberry orange cinnamon rolls. 

Top each roll with some orange zest, and enjoy!