Step 1: Prepare the Brioche Dough

Start by warming the milk to about 110°F – this is the perfect temperature to activate the yeast. If you’re unsure about the temperature, just test it with your finger. It should feel warm but not hot. Stir in the sugar and yeast, and if you’re using active dry yeast, let the mixture sit for about 15 minutes until it becomes frothy. This is a key step because the yeast needs to activate and start working its magic in the dough.

If you’re using instant yeast, you can skip this waiting time and move on to the next step because instant yeast doesn’t require activation.

In a separate bowl, whisk together the eggs and vanilla extract, then add them to the milk mixture. The vanilla adds a subtle sweetness that enhances the overall flavor of the dough.

Now, in the bowl of a stand mixer, combine the flour and kosher salt. Add the wet ingredients and mix everything together on low-medium speed for about 3 minutes, or until the dough starts to form around the hook. If you don’t have a stand mixer, you can use a hand mixer with dough hooks or mix the dough by hand using a wooden spoon.

Step 2: Incorporate the Butter

Once the dough begins to come together, it’s time to add the butter. Slowly add the butter to the dough, one piece at a time. Allow each piece to fully incorporate before adding the next. This process helps create a rich, soft dough that will bake up into the tender, buttery cinnamon rolls you’re after.

After all the butter is incorporated, increase the mixer speed to medium-high and mix for another 8-12 minutes until the dough is smooth, elastic, and slightly tacky. To check if the dough is ready, tear off a small piece and gently stretch it. You should be able to see light through it without it tearing. If it tears, continue mixing for another minute and check again.

Step 3: Let the Dough Rise

Once your dough is ready, transfer it to a lightly greased bowl. Cover it with a clean kitchen towel or plastic wrap and let it proof overnight in the fridge. If you’re in a hurry, let it rise in a warm place for about 1 hour, or until it’s doubled in size. The cold fermentation overnight will develop the flavor of the dough and make the rolls extra fluffy, but the warm rise will work just fine if you’re short on time.

Step 4: Make the Cranberry Orange Jam

While the dough is rising, make the jam. In a medium saucepan, combine the cranberries, sugar, orange zest, orange juice, cinnamon, and salt. Cook over medium heat for about 10-12 minutes, stirring occasionally until the cranberries start to break down. You’ll know it’s ready when the cranberries soften and burst open, releasing their juice.

Once the cranberries have broken down, reduce the heat to low and continue cooking for another 8-10 minutes, stirring frequently, until the jam thickens. The mixture should be thick enough to coat the back of a spoon.

Once the jam has thickened, remove from heat and blend it until smooth using an immersion blender or a regular blender. Let the jam cool completely, then transfer it to a glass jar and chill in the fridge until you’re ready to assemble the rolls.

Step 5: Assemble the Rolls

Once the dough has risen, flour your surface and roll the dough into a rough rectangle about ¼ inch thick. Be careful not to roll it too thin; you want the dough to be sturdy enough to hold the jam filling.

Spread 225g (about 1 cup) of the cranberry orange jam evenly over the dough, leaving about a half-inch border around the edges. You can use a spatula to spread the jam evenly and smoothly.

Now, carefully roll the dough from the long edge, sealing the edge at the end. Once you have your roll, trim off the ends of the dough to make the edges neat. Then, cut the roll into 9 even pieces, each about 1 ½ inches wide. The easiest way to do this is by scoring the dough with a knife and then using dental floss to cut through the dough. This will give you clean, even slices every time.

Step 6: Let the Rolls Rise

Place the rolls in a baking dish (about 10.5″x7.5″), leaving a little space between them so they can expand as they rise. Cover the dish with a towel and let the rolls rise at room temperature for about 30 minutes. While they’re rising, preheat your oven to 350°F.

Step 7: Bake the Rolls

Once the rolls have risen, bake them for 22-25 minutes, or until they’re just barely golden on top. Be careful not to overbake them, as you want them soft and pillowy, with just a hint of golden brown on the edges.

Step 8: Make the Cream Cheese Icing

While the rolls are baking, make the icing. In a medium bowl, combine the cream cheese, melted butter, and sifted powdered sugar. Whisk until smooth and creamy. Add the orange zest to give the icing that lovely citrus note that ties everything together. If the icing is too thick, you can add a teaspoon of milk to loosen it up.

Step 9: Drizzle and Serve

Once the rolls are done baking, remove them from the oven and let them cool for a few minutes. Drizzle the cream cheese icing generously over the top of the warm rolls. The icing will melt slightly, creating a delicious glaze that coats each roll.

These cranberry orange cinnamon rolls are best enjoyed warm, with a cup of coffee or tea. The combination of soft, fluffy dough, tangy-sweet cranberry jam, and creamy icing is a flavor explosion in every bite.