Carefully warm milk over low-medium heat in a small saucepan (warmed between 105F and 115F). Once warmed, remove from heat, pour into a small bowl, and add in yeast, stir and let sit about 10 minutes until bloomed.
In a stand mixer with the dough hook attached, mix together the softened butter, eggs, granulated sugar, salt, and flour until roughly combined. Add in the milk and yeast. Knead dough on medium speed until fully combined, about 4-5 minutes. Cover and let rise for 1 1/2 hours.
While rising, mix together light brown sugar and cinnamon for filling.
Lightly flour a work surface and turn out the dough. Roll gently into a 12x17” rectangle. Spread with 6 tbsp of softened butter, then spread the apple butter (leaving about 1 inch at the borders free), and then sprinkle on cinnamon sugar. Roll dough up starting at the long end. (This part gets messy because of the apple butter— but it is SO worth it!)
Cut into 10 equal pieces. (This part gets messy as well!)
Grease a 9x13” baking pan, or large cast iron skillet. Arrange cinnamon rolls in the pan or skillet. Cover and let rise another hour, or overnight in the fridge (although I don’t recommend letting them rise overnight in a cast iron skillet).
When ready to cook, preheat oven to 350F. Remove from fridge while preheating if you let come to room temperature.
Right before putting it in the oven, drizzle the heavy cream all over the rolls.
Bake for 35-40 minutes until center is cooked through.
While cooking, beat together cream cheese and butter until smooth. Then beat in vanilla, maple syrup, and cinnamon. Add in powdered sugar and salt and beat until combined (will take a few minutes to fully combine butter mix and sugar- it will be thick),
Add in heavy cream 1 tbsp at a time until you get the desired consistency you want for the frosting.
Remove rolls from oven, cool 5-10 minutes, and then frost. Enjoy!