For the dough:
- ½ cup milk
- 1 packet (2 ¼ tsp) active dry yeast
- ¼ cup sugar + ¼ tsp, divided
- 7 Tbsp unsalted butter, softened
- 1 egg + 1 egg yolk at room temperature
- 1 tsp vanilla extract
- ¼ tsp cinnamon
- ½ tsp salt
- 3 ½ cups bread flour
For the cinnamon filling:
- 1 cup dark brown sugar
- 3 Tbsp cinnamon
- ⅓ cup butter, softened
For the cream cheese icing:
- 4 oz cream cheese, softened
- 1 ½ cups confectionaire’s sugar
- 1 tsp vanilla extract
- 1 Tbsp milk
- Start by making your dough. Heat milk to 100-110°F (about 45 seconds-1 minute 30 seconds in the microwave). If you don’t have a thermometer, you can insert a (clean!) finger into the milk, which should feel warm but not scalding hot. Stir in yeast + ¼ tsp sugar and allow to sit for 10 minutes until the yeast activates and becomes foamy.
- In a stand mixer with the dough hook attachment, add in the egg, egg yolk, vanilla, ¼ cup sugar, cinnamon, salt, yeast mixture and flour, and mix until combined. It’ll be crumbly at this point and not fully come together.
- Begin adding softened butter a Tbsp at a time. Allow each piece of butter to fully incorporate into the dough before adding more. Once butter has been fully incorporated, continue mixing until dough is uniform and elastic.
- Transfer dough to a large greased bowl and cover with a towel or plastic wrap. Allow the dough to rise until it has doubled in size, around 2 hours.
- Meanwhile, make the cinnamon filling: Add ingredients to a bowl or a stand mixer with the paddle attachment and mix to combine.
- After the dough has risen, prepare a cookie sheet with parchment paper.
- On a floured cutting board or a silicone baking mat, roll the dough to about 12×9 inches and spread the cinnamon filling across it, leaving ½ inch bare around the perimeter of the dough.
- Using water, wet the longest bare dough edge nearest you and then roll the dough tightly into a log.
- Refrigerate the dough for 20-30 minutes.
- Cut the log in half lengthwise to expose the layers then cut the strips in half lengthwise again. This should leave you with four long pieces of dough.
- Wet one side of each piece and pinch one end together. Starting with the pinched end, tightly roll each piece with the wet side facing in, so that the dough will stick to itself. Pinch and wet the other end and tuck it underneath the roll to keep it from unraveling.
- Once you’ve made your four rolls, place them evenly spaced apart on your cookie sheet.
- Preheat your oven to 350°F and allow your rolls to rise for 30 more minutes.
- Bake the rolls for 20-30 minutes.
- Meanwhile, make the icing: Place 1½ cups confectionaire’s sugar and the cream cheese in a mixer bowl and beat well to combine. Add the vanilla and the milk. For thicker icing, add more confectionaire’s sugar, a Tbsp at a time until you reach the desired consistency. Allow the rolls to cool slightly before topping with the cream cheese icing.
- Prep Time: 30 minutes
- Cook Time: 30 minutes
- Category: Breakfast
- Method: Baking
- Cuisine: Ashkenazi