For the Brioche Dough:

1. Activate the Yeast:
   Warm the milk to 110°F. Stir in sugar and yeast. If using active dry yeast, let it sit for 15 minutes until frothy. If using instant yeast, proceed immediately.
2. Combine Wet Ingredients:
   Mix the eggs and vanilla into the milk and yeast mixture until well combined.
3. Prepare Dry Ingredients:
   In the bowl of a stand mixer fitted with a dough hook, combine the flour, orange zest, and salt.
4. Incorporate Wet Ingredients:
   Gradually pour the wet mixture into the dry ingredients. Mix on low-medium speed for about 3 minutes until a dough ball forms around the hook.
5. Add Butter:
   Add the butter one piece at a time, allowing each to fully incorporate before adding the next.
6. Knead:
   Increase the mixer speed to medium-high and knead for 8-12 minutes. The dough should pass the “windowpane test” — when stretched, it should become thin enough to see light through without tearing.
7. First Proof:
   Transfer the dough to a greased bowl, cover, and proof overnight in the fridge. Alternatively, let it rise in a warm place for 1 hour until doubled in size.

For the Cinnamon Orange Cranberry Jam:

1. Cook the Cranberries:
   In a medium saucepan, combine cranberries, sugar, orange zest, orange juice, cinnamon, and salt. Cook over medium heat, stirring frequently, for 10-12 minutes until the cranberries begin to break down.
2. Thicken the Jam:
   Lower the heat and cook for another 8-10 minutes, stirring often, until the mixture thickens.
3. Blend and Cool:
   Remove from heat and blend the mixture until smooth using an immersion blender or a standard blender. Cool completely and store in the fridge until needed.

Assembly:

1. Roll Out the Dough:
   On a lightly floured surface, roll the dough into a rectangle about ¼ inch thick.
2. Spread the Jam:
   Evenly spread 225 g (about 1 cup) of cranberry jam over the dough.
3. Shape the Rolls:
   Roll the dough tightly from the long edge and seal the seam. Trim the ends and cut into 9 equal pieces using unflavored dental floss for clean cuts.
4. Second Proof:
   Arrange the rolls in a greased baking dish (at least 10.5″x7.5″). Cover and let them rise at room temperature for 30 minutes.
5. Bake:
   Preheat the oven to 350°F. Bake the rolls for 22-25 minutes until lightly golden.