Prepare the Apple Filling & Topping: In a medium pan over medium-high heat, combine all apple filling ingredients. Cook for 8–10 minutes, stirring occasionally, until the apples are tender and the mixture has thickened. If the liquid evaporates too quickly, add a splash of cider or water to maintain a saucy consistency.

Make the Cinnamon Roll Dough: In the bowl of a stand mixer, whisk together melted butter, warm milk, eggs, granulated sugar, instant yeast, and salt. Gradually add the flour, mixing until a soft dough forms. Attach the dough hook and knead for 7–10 minutes until the dough is smooth and elastic.

First Rise: Lightly grease the dough with cooking spray, cover the bowl with a kitchen towel, and let it rise for about 1 hour, or until doubled in size.

Prepare the Crisp Topping: In a medium bowl, combine flour, oats, brown sugar, salt, and cinnamon. Cut in the cold butter using a pastry cutter or your fingers until the mixture resembles coarse crumbs. Set aside.

Make the Caramel Apple Cider Sauce: In a small saucepan, melt butter over medium heat. Stir in brown sugar, cinnamon, salt, apple cider, and vanilla extract. Bring to a simmer and cook for 2–3 minutes until the sauce thickens slightly. Remove from heat and stir in heavy cream.

Prepare the Cinnamon Filling: In a small bowl, beat together softened butter, brown sugar, cinnamon, nutmeg, salt, and vanilla extract until smooth and creamy.

Assemble the Rolls: Once the dough has risen, punch it down and turn it out onto a floured surface. Roll the dough into a 16×12-inch rectangle. Spread the cinnamon filling evenly over the dough, leaving a small border around the edges. Spoon the apple filling over the cinnamon layer. Starting from the long edge, roll the dough tightly into a log.

Slice and Arrange: Cut the rolled dough into 12 equal slices. Place them in a greased 9×13-inch baking dish.

Second Rise: Cover the baking dish with a kitchen towel and let the rolls rise for 30–40 minutes, or until puffy and nearly doubled in size.

Bake: Preheat the oven to 350°F (175°C). Pour the heavy cream evenly over the risen rolls. Bake for 35–40 minutes, or until the rolls are golden brown and cooked through.

Prepare the Frosting: While the rolls are baking, beat together cream cheese, powdered sugar, vanilla extract, salt, cinnamon, and milk or heavy cream until smooth and creamy.

Finish the Rolls: Once the rolls are baked, remove them from the oven and let them cool for a few minutes. Spread the cream cheese frosting over the warm rolls. Top with the prepared crisp topping and additional apple filling. Serve warm and enjoy!