In the bowl of a stand mixer, combine the yeast with the warmed milk and the sugar. Let sit for about 5 minutes until the liquid looks foamy.
Add the butter, salt, cinnamon, eggs and flour to the bowl and begin to mix the dough with a dough hook attachment. Allow the dough to slowly come together, scraping down the sides of the bowl as needed.
If the dough looks soft and is not forming a ball, add more flour, about 1/4 cup at a time, until the dough begins to form. The dough should pull away from the sides of the bowl and be easy to handle and mold with your hands.
Place the dough into a large greased bowl and cover. Set the bowl in a warm place and let the dough rise for 1 1/2 to 2 hours.
While the dough is rising, begin making your filling by very finely dicing the apples.
Sauté the apples in a large skillet along with the butter.
Transfer the apples to a medium sized bowl once they begin to soften.
Using the same skillet that you cooked the apples in (with the remaining butter), add the brown sugar and cinnamon and mix constantly over medium heat to melt the sugar completely.
Allow the sugar to boil for about 8 minutes and then turn off the heat. Slowly add the cream to the pan, whisking constantly.
The cream will cause the caramel to bubble and steam so be careful but continue to whisk the mixture.
Pour half of the caramel over the apples and reserve the remaining caramel for the top of the cinnamon rolls.
Once the dough has proofed, turn it out onto a well floured surface.
Roll the dough to about 1/4 inch thick.
Spread the caramel apple filling onto the dough using an offset spatula.
Roll the dough from the bottom upward into a nice log.
Slice the dough log into 2 inch sections using a serrated knife.
Place the cinnamon rolls into a greased 8" cake pan, leaving a little bit of space between the rolls for the dough to rise. Cover the pan and set it in a warm place for another 30 minutes
Once the cinnamon rolls have doubled in size, bake in a 350 ̊F oven for about 30 minutes or until they turn golden brown.
Remove the rolls from the oven and allow to cool slightly in the pan
Flip the cinnamon rolls out of the pan and onto a serving tray or plate. Drizzle with the remaining caramel and serve while warm!