Step 1: Prepare the Cranberry Filling

1. Combine all cranberry filling ingredients in a medium saucepan over medium-high heat.
2. Bring to a boil, stirring frequently, until cranberries burst (3-5 minutes).
3. Reduce heat to medium and simmer for 10-15 minutes, stirring occasionally, until thickened. Set aside to cool.

Step 2: Make the Dough

1. Melt the butter in a microwave-safe bowl. Add the milk and heat for 15-30 seconds until warm but not hot. Stir in the yeast and let it sit for 1-2 minutes.
2. In a mixer bowl, combine 3 cups of flour, sugar, and salt. Pour in the milk mixture and add the egg. Beat with the paddle attachment until combined. Add orange zest and mix.
3. Switch to the dough hook and add the remaining 1 cup of flour gradually. Knead for 5 minutes until the dough is smooth and elastic. Cover and let rest for 10 minutes.

Step 3: Prepare the Orange Filling

1. In a small bowl, mix softened butter, sugar, and orange zest until well combined.

Step 4: Assemble the Rolls

1. Roll out the dough on a floured surface into a large rectangle (about 12×18 inches).
2. Spread the orange filling evenly over the dough. Spoon the cranberry filling on top, leaving space around the edges.
3. Roll the dough tightly into a log. Pinch the seam to seal.

Step 5: Cut and Rise

1. Cut the log into 1 1/2-inch rolls (about 12 pieces).
2. Place the rolls in a greased 9×13 baking dish. Cover with a towel and let rise in a warm place for 1 hour.

Step 6: Bake

1. Preheat the oven to 350°F (175°C).
2. Bake the rolls for 20-30 minutes until golden brown on top and cooked through.

Step 7: Make the Glaze

1. In a bowl, mix melted butter, milk, vanilla extract, powdered sugar, orange juice, and zest until smooth.

Step 8: Glaze and Serve

1. Drizzle the glaze over the rolls while they are warm but not hot.
2. Serve warm or at room temperature. Enjoy!