Soft, fluffy cinnamon rolls filled with warmly spiced, tender apples and brown sugar-cinnamon, finished with a silky salted caramel vanilla icing—like apple pie meets a classic cinnamon roll.
Whisk warm milk, 2 tablespoons of the granulated sugar, and the yeast in the bowl of a stand mixer; cover and let sit 5–10 minutes until foamy.
Add the remaining granulated sugar and the softened butter; mix on medium speed until the butter is slightly broken up.
Add about 1 cup of the flour, the eggs, and salt; mix on low for 30 seconds, scraping down the bowl as needed.
Add the remaining flour and mix on medium until the dough comes together and pulls away from the sides. If very sticky, add more flour 1 tablespoon at a time.
Knead with a dough hook or by hand until smooth and elastic. Place in a lightly greased bowl, cover, and let rise until doubled, about 1–2 hours.
While the dough rises, pre-cook the apples: Cook the peeled, chopped apples in a skillet with a splash of water for about 5 minutes, just until beginning to soften; cool completely.
Punch down the risen dough and roll into a 12×18-inch rectangle.
Spread softened butter over the dough; sprinkle evenly with brown sugar and cinnamon. Distribute the pre-cooked apples over the filling.
Tightly roll the dough into a log and cut into 12 rolls.
Arrange rolls in a greased or lined 9×13-inch pan; cover and let rise until puffy.
Bake until the rolls are lightly browned, tenting loosely with foil halfway if needed so the tops don’t over-brown before centers are baked through.
For the icing, whisk confectioners’ sugar, vanilla, milk, and warmed salted caramel until smooth. Drizzle over warm rolls and serve.