Apple Cinnamon Rolls with Jack Daniels-Cream Cheese Icing

Apples, Bread, Breakfast, Pastry

Apple Cinnamon Rolls with Jack Daniels Cream Cheese Frosting

From the archives

It’s September! The 9th month of the year is the gateway to sweatshirts, chili, football, and all things pumpkin. But before there’s pumpkin and Halloween candy, there are apples.

This month, Rachel is throwing an Apple a Day party – a group of fabulous bloggers sharing their favorite apple recipes. And my contribution? Breakfast. But not just any breakfast. It’s cinnamon roll meets apple pie meets Jack Daniels.

The cinnamon rolls are dressed up for fall with vanilla bean, brown sugar, apples, and whiskey and then topped with a cream cheese glaze scented with just a little bit more whiskey. It will take you longer to read the recipe title aloud than it will to inhale a cinnamon roll and lick your fingers clean. I speak from experience.

Apple Cinnamon Rolls with Jack Daniels-Cream Cheese Icing

Happy September! And seriously. Make those cinnamon rolls this weekend.

Apple Cinnamon Rolls with Jack Daniels Cream Cheese Icing

Celebrate fall with cinnamon rolls filled with apples, brown sugar, and whiskey.


  • For the Dough:
  • 4 large egg yolks
  • 1 large whole egg
  • 1/4 cup sugar
  • 2 tsp vanilla bean paste or extract (or the scrapings from 1 vanilla pod)
  • 6 Tbsp unsalted butter, melted
  • 3/4 cup buttermilk
  • 4 cups flour (20 oz), plus more for dusting surface
  • 1 pkg (2 1/4 tsp) instant yeast
  • 1 tsp salt
  • Vegetable oil or cooking spray
  • For the Filling:
  • 4 Tbsp butter
  • 2 apples (I used Braeburn), peeled and diced into 1/4-inch cubes
  • 1 cup packed dark brown sugar, divided
  • 1 Tbsp ground cinnamon
  • 2 Tbsp Jack Daniels (optional but highly recommended; can omit)
  • 1 tsp vanilla
  • Pinch salt
  • For the Icing:
  • 2.5 oz cream cheese, softened
  • 2 Tbsp milk
  • 2-3 tsp Jack Daniels (optional; can replace with milk)
  • 1 cup powdered sugar


  1. Make the dough: In the bowl of a stand mixer fitted with the dough hook, beat the egg yolks, whole egg, sugar, butter, vanilla, buttermilk and half the flour together until well combined. Add yeast, salt, and the next 1 1/4 cup flour (leaving about 3/4 cup remaining) and knead on low for 5 minutes.
  2. Add additional flour by the spoonful if necessary - you want the dough soft and moist but not overly sticky. Knead another 5 minutes until the dough clears the sides of the bowl (but might still stick to the bottom a bit).
  3. Transfer dough to a lightly greased, large bowl and let double, 2-2.5 hours.
  4. Just before the dough is finished, make the filling. Melt the butter in a large saute pan and add the diced apple. Crumble 1/2 cup of brown sugar over top and stir in the cinnamon, a pinch of salt, and Jack Daniels. Simmer for 10 minutes, until thick and bubbly. Remove from heat, stir in vanilla, and set aside to cool.
  5. Spray or butter a 9-inch pan. Turn out the dough onto your lightly floured work surface. Stretch and roll the dough into a ~12x18 rectangle with the long edge nearest to you.
  6. Sprinkle the remaining 1/2 cup brown sugar over the dough, leaving the top 1-inch bare. Spread the cooled apple mixture over the dough.
  7. Starting with the edge of the dough closest to you, roll the dough into a cylinder and pinch the the seam to seal. Gently press, squeeze, and stretch the roll to get an even thickness.
  8. Cut the roll into 1 1/2-inch slices and place in the baking dish (you'll get 12 rolls). Cover tightly with foil or plastic wrap and refrigerate overnight.
  9. Place the rolls in the oven with the heat off. Fill a shallow pan 2/3 full of boiling water and place it on the rack below the rolls. Close the oven and let the rolls rise for ~30 minutes.
  10. Remove the water pan and rolls from the oven and preheat the oven to 350.
  11. Bake rolls on the middle rack for 25-30 minutes, until golden brown.
  12. While the rolls are cooling, beat the cream cheese, milk, Jack Daniels (to taste, 1-2 tsp at a time), and powdered sugar together until smooth. Drizzle over the rolls and serve.
  13. Leftovers can be stored in the fridge, tightly covered. Rewarm in the microwave for best results.


Yields: 12 rolls

Adapted from Overnight Cinnamon Rolls