Make the Apple Filling & Topping

Combine the diced apples, ¼ cup butter, ½ cup light brown sugar, lemon juice, cinnamon, nutmeg, ground cloves, allspice, salt, and vanilla in a medium pan over medium-high heat. Stir occasionally for about 8–10 minutes until the apples start to soften and juices run.

If liquid evaporates before apples are tender, add a splash of water or cider. Once apples are soft, mix 2 tsp cornstarch with 2 tsp water to make a slurry, add to the pan, and cook for another 30–60 seconds until mixture thickens like jam. Remove from heat and set aside.

Make the Dough & First Rise

In a stand mixer bowl, whisk together melted butter, warm milk, beaten eggs, sugar, yeast, and salt.

Switch to paddle attachment, add flour, and mix on low until flour disappears and dough becomes shaggy. Let rest 5 minutes.

Replace paddle with dough hook and knead on low (setting 1–2) for 5–7 minutes until dough becomes smoother, more elastic — though still slightly slack.

Transfer dough to the same bowl (sprayed with nonstick spray), cover, and let rise for about 1 hour — until doubled in size and a finger-indent holds.

Prepare Crisp Topping

Preheat oven to 350 °F (≈ 175 °C). Line a baking sheet with parchment. In a bowl, whisk flour, oats, brown sugar, salt, and cinnamon. Cut cold butter into chunks and use a pastry blender (or two forks) to cut the butter into dry ingredients until crumbly.

Spread the mixture evenly on the baking sheet. Bake for 12–16 minutes, stirring halfway through and redistributing the edges toward the center to avoid burning. Once golden and crunchy, set aside to cool.

Make Caramel Apple Cider Sauce

In a medium bowl, stir together softened butter, dark brown sugar, cinnamon, salt, boiled apple cider, vanilla, and heavy cream until smooth.

Lightly spray a 9×13″ (or similar) baking pan with nonstick spray. Spread this thick sauce evenly on the bottom.

Make Cinnamon Filling

In a mixing bowl, beat together softened butter, light brown sugar, cinnamon, nutmeg, a pinch of salt, and vanilla on medium-high speed until creamy and smooth.

Assemble the Rolls — First Roll & Filling Stage

Turn risen dough onto a well-floured surface. Roll it into a large rectangle, about 14 by 22 inches (or up to 15 × 24 if space allows).

Evenly dot the cinnamon filling over the rolled dough. Use an offset spatula to gently spread it almost to the edges.

Evenly scatter about 1 ½ cups of the prepared apple filling on top of the cinnamon layer. It doesn’t have to be perfectly even.

Shape the Rolls

From the long side of the rectangle, slice strips about 1¾ inches wide.

Roll each strip up into a log and place each resulting roll seam-side down onto the prepared pan over the caramel sauce. For the two end strips (which may be smaller), roll them together to make one full-sized roll. Place any smaller rolls in the center of the pan so all bake evenly.

Second Rise (Proofing)

Loosely cover the pan with a kitchen towel and let rolls rise for 30–40 minutes in a warm spot, until puffy. Use the “finger-indent test” (if an indent remains, they’re ready). Meanwhile preheat oven to 350 °F (≈ 175 °C).

Bake the Rolls

Once risen, gently pour the warmed heavy cream (from the cinnamon-filling ingredient list) over and in between the rolls.

Bake for 40–46 minutes, until golden brown and centers look set. For best accuracy, insert an instant-read thermometer into the center of one middle roll — it should read 205–210 °F. If the thermometer shows raw dough, bake a few extra minutes.

Make the Frosting & Final Toppings

While the rolls bake, beat together softened cream cheese, powdered sugar, vanilla extract, salt, cinnamon, and 2–3 tbsp milk or heavy cream on medium-high speed until smooth and creamy. Adjust cream to your desired consistency.

As soon as rolls come out of the oven, spread frosting generously over them. Then top with a spoonful of the reserved warm apple filling and sprinkle the cooled crisp topping for added crunch.

Serve & Store

Serve warm, straight from the pan — these are best fresh from the oven. Leftovers? Store in an airtight container in the fridge for 2–3 days. Reheat gently before serving for the best texture.