Step 1

For the dough: Make sure the milk is warmed up to around 110°F. I like to do this by placing my cold milk in a microwave safe vessel and microwaving it for 45-50 seconds (it should be warm as if you are giving it to a baby and not scalding). In the bowl of a stand mixer, add in the sugar and warmed milk. Then sprinkle the yeast on top. Let sit for 7-10 minutes for the yeast to activate- the mixture will be bubbly and fragrant.

Step 2

Next, add in the melted butter, eggs, flour, and salt. Attach dough hook attachment to mixer and knead on medium speed until the dough begins to come together, about 6-8 minutes. Look for the dough to be smooth. If your dough is sticking to the bowl, add in a tablespoon more of flour, only if needed. Alternatively, if you are not using a stand mixer- you can knead the dough by hand for 10 minutes on a lightly floured surface.

Step 3

Shape the dough into a ball and place it into a lightly greased large bowl. Cover the bowl tightly with plastic wrap and a clean towel/linen- let the dough rise in a warm environment until it doubles in size, about 1 1/2 hours or longer depending on the temperature of your environment.

Step 4

Once the dough has risen, punch the dough down and turn it out onto a lightly floured surface work area. Roll the dough out into a rectangle, about 15×10 inches, now let’s prepare the filling.

Step 5

For the filling: Spread the softened butter over the dough, leaving a slight margin around the edges. I like to use my hands (use disposable gloves, if desired) to do this. In a small bowl, combine the brown sugar and peach preserves together. The mixture should resemble a thick paste. Spread the mixture over the buttered dough and rub into the butter, leaving a slight margin around the edges. Lastly, evenly sprinkle the cinnamon all over the top and use your hand to gently pat it into the mixture.

Step 6

Rolling the dough: Roll up the dough into a tight log starting from the longest side with the seam side down. While in log position, use your hands to carefully stretch out the log, if needed. Then pinch the seam to nicely seal in the edges as much as you can. I like to cut off a bit of the ends of the dough because they are not as full in size as the other sections.

Step 7

Cutting the dough: Use a large sharp knife or unscented floss to cut the log crosswise into 12 pieces. You can also cut the log into 9 pieces for slightly larger rolls.

Step 8

Resting the rolls: Line a 13×9 inch baking dish with a piece of parchment paper (this helps just in case any of the filling leaks out). Add the rolls into the baking dish and cover tightly with plastic wrap. Transfer the dish into the refrigerator to rise overnight, 8-10 hours. >>> Alternatively, to make rolls on the same day, allow the rolls to rise again in a warm environment for another 1-2 hours until puffy. Then bake the cinnamon rolls as directed in the step below.

Step 9

Baking the rolls: Remove the rolls from the fridge and let the rolls sit out before baking to come back up to room temperature until puffy, about 1-2 hours. Preheat the oven to 350°F. Remove the plastic wrap and bake the rolls until lightly golden brown, about 30 minutes. While the rolls bake, prepare the icing.

Step 10

For the icing: Using a stand mixer fitted with the paddle attachment (or electric hand mixer), beat the butter and cream cheese together until light and fluffy, about 3-4 minutes. Add in the powdered sugar and continue beating until well incorporated. Then add in the vanilla paste/extract and continue mixing until everything is fully combined and smooth.

Step 11

Once the rolls are done baking, allow them to cool for 5 minutes before icing.

Step 12

For the peach cobbler topping: In a small saucepan over medium-low heat, add in the sliced peaches, butter, brown sugar, cinnamon, nutmeg, and salt. Carefully stir (to avoid overly breaking the peach slices) the mixture together to combine and cook until the sugar begins to dissolve, about 2-3 minutes. Once the mixture is nice and warm and sugar has dissolved, remove from heat. If using, pour in the bourbon and stir to combine. Then allow to cool for 5 minutes.

Step 13

Top each iced cinnamon roll with a spoonful of the peach cobbler mixture. Then garnish the peach cobbler cinnamon rolls with the crushed shortbread cookies. Serve and enjoy!