For the dough: In a glass measuring cup, heat the milk, in the microwave, until it reaches 105-110°F. Whisk in the yeast and 1 teaspoon of the granulated sugar. All the mixture to sit for 5-10 minutes, or until it is bubbly and “active”.

While the yeast mixture sits, whisk together the remaining granulated sugar, eggs, vinegar, and vanilla extract in the bowl of a stand mixer until combined. In a separate medium bowl, stir together the gluten free all-purpose flour, tapioca flour (or tapioca starch), arrowroot, coarse Kosher salt, baking soda, and cream of tartar. Set aside.

Once the yeast mixture is ready, place it in the bowl of the stand mixer fitted with the paddle attachment. Add the dry ingredient mixture to the bowl, and turn the mixer on low until the wet and dry ingredients are well combined. Scrape the bottom of the bowl, and add the butter. Turn the mixer on medium, and mix until well combined. Turn the mixer off and scrape down the bowl. Turn the mixer on high, and mix for about 5-8 minutes. NOTE: The mixture will be sticky.

Place the mixture into a medium, well-oiled bowl. Wrap tightly in plastic wrap, and place in the refrigerator for at least 8 hours or overnight to rise.

While the dough is rising, make the apple mixture. Stir together apples, granulated sugar, lemon zest and juice, butter, cinnamon, nutmeg, cloves, salt, and vanilla in a small saucepan over medium heat. Cook, stirring often, for 15 minutes, until the apples are tender and beginning to break apart. Set aside to cool

For the cinnamon sugar filling, melt the butter and set aside. Toss together the granulated sugar and cinnamon in a small bowl and set aside.

Once the dough has risen in the refrigerator for at least 8 hours, remove from the refrigerator and turn out onto a well floured surface (be sure to use gluten free 1:1 all purpose flour). Roll the dough into a rectangle that is about ¼ inch thick, measuring approximately 15 inches by 12 inches. Spread the melted butter onto the dough, and then sprinkle with the cinnamon sugar mixture, leaving about an inch of dough on all edges. Next spread the apple mixture over the cinnamon sugar mixture.

Working from one end of the dough across to the other side, gently roll the dough into a pinwheel shape. Trim the ends of the dough. Next, cut the pinwheel into 12 even pieces by cutting the dough in half, and then cutting each half in half, creating quarters. Finally, cut each quarter into 3 equal pieces. Place the pinwheels into a parchment lined 9x12 inch baking pan.

Cover the pan with a warm, damp cloth, and let rise for 30-45 minutes. When the dough is ready, preheat the oven to 350°F. Remove the damp cloth and place the pan in the oven. Bake for 20-25 minutes, or until lightly browned. Remove from the oven, and let cool for about 15-20 minutes. While the rolls are cooling, make the icing.

To make the icing, whisk together cream cheese and butter in a small to medium bowl. Add powdered sugar, vanilla extract, whisking until well combined and smooth. Spread icing evenly over the cinnamon rolls and serve! These cinnamon rolls are best served fresh, but if you are planning to serve at a later time or the next day, reserve the icing until ready to serve.

Since the icing contains cream cheese, it will need to be refrigerated, so if you are planning to only serve a few at a time, ice cinnamon rolls as they are ready to serve.