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 (about 3–5 minutes).
3. Reduce heat to medium and simmer for an additional 10–15 minutes 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 about 15–30 seconds until warm but not hot.
2. Stir in the yeast and let it sit for about 1–2 minutes.
3. In a mixing bowl, combine 3 cups of flour, sugar, and salt. Pour in the milk mixture and add the egg. Beat with a paddle attachment until combined.
4. Add orange zest and mix well.
5. Switch to a dough hook and gradually add the remaining cup of flour while kneading for about 5 minutes until smooth and elastic.
6. Cover and let rest for about 10 minutes.

Step 3: Prepare the Orange Filling

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 (approximately 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 and pinch to seal.

Step 5: Cut and Rise

1. Cut the log into rolls about 1½ inches thick (approximately 12 pieces).
2. Place rolls in a greased 9×13 baking dish. Cover with a towel and let rise in a warm place for about an hour.

Step 6: Bake

Preheat your oven to 350°F (175°C). Bake rolls for about 20–30 minutes until golden brown on top.

Step 7: Make the Glaze

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

Step 8: Glaze and Serve

Drizzle glaze over warm rolls before serving.