1. In the bowl of a stand mixer fitted with a dough hook, whisk together the warm milk, granulated sugar and yeast. Allow everything to sit for 5 minutes until the yeast becomes foamy. If it does not foam up, start again with fresh yeast!
2. Add in 1 cup of the flour, the salt and 2 tablespoons of softened butter. Mix together on low until things start to come together. With the mixer running on low, add in the eggs, one at a time. Add in the remaining flour to make 2 3/4 cups, then mix on medium-high until everything is combined. Run the mixer for 3 minutes; the dough should pull away from the sides of the bowl. If it is still sticking to the bowl, add in the remaining 1/4 cup of flour, a few tablespoons at a time. Remove the dough, spray the inside of the bowl with nonstick spray and replace the dough. Cover it with a damp towel and allow it to rise in a warm spot for 1-2 hours, or until doubled in size.
3. While the dough is rising, prepare the apple filling. Combine the diced apples, cinnamon and sugar together in a small mixing bowl. Set aside.
4. Split the dough into 2 pieces (use a kitchen scale or just eyeball it). Keep one half of the dough covered in the bowl, while you place the other half on a lightly floured surface. Roll out the dough to a 9 x 15″ rectangle, then smear 1/4 cup of softened butter all over the dough. Sprinkle the 1/2 tsp ground cinnamon across the dough.
5. Using a sharp knife or pizza cutter, slice the dough into 4 equal strips. Sprinkle a few tablespoons of the apple filling on one of the strips, then place another strip on top. Place more apples on top of the doubled up strip, then place another strip on top. Repeat with the remaining two strips until you have a tall stack of dough. Slice the dough into 6 equal pieces; if some apples spill out you can add them on to the prepared loaf later!
6. Place the little stacks of dough into a standard-sized loaf pan lined with parchment paper. Repeat the process with the second half of dough and remaining apple filling, placing the second half of stacks into another prepared loaf pan. Cover the pans with a damp towel again, letting them rise for another 1 hour, or until puffed up.
7. Preheat the oven to 350 F. While the dough is rising, prepare the caramel sauce. In a small saucepan over medium heat, whisk together the brown sugar, heavy cream and butter until the butter is melted and the mixture begins to simmer. Reduce the mixture to low and allow the caramel sauce to simmer for 15 minutes or until thickened. Remove from heat and set aside while the bread bakes.
8. When the oven is preheated, place both pans into the oven to bake for 30 minutes or until golden brown on top. Check to make sure the bread is fully baked by wiggling the middle piece of the bread to see if it looks doughy or fully baked. If it is doughy, the bread needs to be baked for another 5 minutes. Remove the loaves from the oven and allow them to rest for 5 minutes before removing them from the pan to a cutting board. Drizzle the caramel sauce all over the loaves and serve!

Leftover loaves can be stored in an airtight container for up to 3 days. Un-glazed loaves can be stored in the freezer for up to 2 months, after being fully cooled.