Apple Pie Filling (Make up to 2 days ahead)

Cup of Yum
1. In a large skillet, melt butter (2 TBL) and add brown sugar (3 TBL), apples (3 cups), cinnamon (½ TBL) and vanilla (½ TBL). Saute apples, stirring occasionally until apples are tender and soft. Remove from heat and store in an airtight container until ready to use.

Make Cinnamon Roll Dough

1. In a small saucepan add butter (⅓ cup), milk (1 cup), sugar (¼ cup) and kosher salt (½ teaspoon), stirring until warmed, not higher than about 120° F. Careful it can go from warm to hot fast. If too hot (greater than 130° F), let sit until cools slightly. Butter may not be completely melted, but that's okay.
2. While milk is warming (or cooling) place 2 cups of bread flour into bowl of a stand mixer with batter attachment, add yeast and mix on low to combine.
3. Slowly pour in warmed milk mixture into flour and yeast mixture, mixing on low. It will be thick and sticky.
4. With mixer on low, add room-temperature eggs and the remaining 2 ¼ cups of flour, mixing well to combine. *Forget to take your eggs out, place in bowl of warm (not hot) water for 5-7 minutes)
5. Next, replace paddle attachment with J hook for kneading; knead the dough for 5-10 minutes on a low setting, until dough is smooth and elastic.*If the dough is too sticky (sticking to the sides of the bowl) after a few minutes, then add a tablespoon more of flour at a time, until it's tacky, but not sticky. The dough should be soft, elastic and smooth.
6. Don't have a kneading attachment? Then turn dough onto floured surface and knead for the same amount of time.
7. Spread a teaspoon of unflavored oil into a medium bowl and, using a paper towel spread it all over the bowl. Plop your cinnamon roll dough into the bowl and turn to "grease" top and bottom, seal with plastic wrap and set in a warm place for 15 minutes to rest. Note at this point, you may cover the dough well and store in the fridge overnight, proceed with recipe in the morning.See notes for how to create a warm proofing place.

Make Cinnamon Roll Filling (Make 1-2 days ahead)

1. Meanwhile, in a small mixing bowl or stand mixer, mix together softened butter (½ cup), packed brown sugar (¼ cup), granulated sugar (¼ cup) and cinnamon (1 ½ tablespoons) and kosher salt (¼ teaspoon). Mix on medium-high speed until smooth and creamy, set aside.

Roll out Cinnamon roll dough

1. Once your dough has rested, it will be easy to roll. Like playdough. Turn dough onto a lightly floured surface (I like using my silpat with measuring gauge) and roll using a rolling pin into a 18x21 inch (roughly) rectangle.
2. Using an offset spatula, spread the cinnamon roll filling evenly over the top of the dough, leaving ½-1 inches around the edges.
3. Remove 2-3 tablespoons of the apple pie filling and set aside if adding to the frosting. Spread the remaining completely cooled apple pie filling over the cinnamon roll filling, keeping it a little heavier towards the bottom of the dough.
4. Roll, from the long side tightly and pinch edges to seal, using a little water on seams if needed. Note that some of the filling may ooze out, that’s okay, save it and we’ll tuck it back in.
5. Cut ends off if uneven and then using a serrated knife or dental floss, cut into 12-15 evenly sized rolls and place in a well-greased or parchment-lined 9×13 pan. Spoon any extra apples that oozed out over the tops of the rolls.
6. Cover cinnamon rolls with plastic wrap and allow to rise in a warm place for about 45 minutes, until almost double. Make sure your oven is turned off if rising in the oven.
7. Preheat oven to 400° (205° C) for regular pans; 375° F (190° C) if using a dark or glass pan.
8. Once doubled in size, remove plastic wrap bake rolls for about 18-25 minutes until slightly golden in a preheated oven.
9. While baking or during rising time, make the frosting.

Make Spiced Cream Cheese Frosting (Make 1-2 days ahead)

1. In the bowl of a stand mixer or hand mixer, beat room temperature butter (¼ cup) and cream cheese (4 ounces) on medium-high for 4 minutes until light and fluffy. Reduce speed to low, and add powdered sugar (1 cup), vanilla (2 teaspoons), and 1 teaspoon apple pie spice (or other), beat until smooth, light, and fluffy.
2. Add a little milk or cream if a thinner consistency is desired. Set aside until ready to use. (May be made 2 days ahead), cover and refigerate.
3. Remove cinnamon rolls from the oven when golden brown and the middle rolls spring back when lightly touched. Everyone likes their cinnamon rolls baked differently, for softer, gooey rolls bake on the lower side, for more firm rolls bake on the longer side.
4. Allow the rolls to cool for about 15-20 minutes before spreading the frosting on the tops. Or cool completely and serve with frosting on the side!