Apple Pie Cinnamon Rolls

The fluffiest cinnamon rolls with apple pie filling and a caramel drizzle. Perfect for Christmas morning!



For the Cinnamon Rolls:

  • 2 1/4 tsp active dry yeast
  • 3/4 cup warmed milk (regular or non-dairy) (warmed between 100-110℉)
  • 1/4 cup honey
  • 4 eggs (room temperature)
  • 4 cups all purpose flour (568g)
  • 2 tsp kosher salt
  • 10 tbsp unsalted butter, room temperature, cut into 1" cubes (142g)
  • 1 cup pecans (raw), roughly chopped

For the Filling:

  • 2 tbsp unsalted butter
  • 1/2 cup brown sugar
  • 1 1/2 tbsp cinnamon
  • 2 cups chopped apples (skin left on is fine, I like honeycrisp)

For the Date-Caramel Sauce:

For the Caramel Icing:


  1. If using active dry yeast, add this to a bowl first followed by the warmed milk (between 100-110℉). This step ensures that the active dry yeast is good to go. If you're using instant yeast, you can skip this step and add it with the flour and salt in step 3.
  2. Once you can see that the yeast is foamy and alive, add the honey and eggs and mix. (If using instant yeast, just whisk together the honey and eggs with the milk).
  3. Grease a large bowl for the dough. In a stand mixer fitted with the paddle attachment, mix the flour and salt on low to combine. With the mixer still on low, add the egg/milk mixture.
  4. While the mixer is still running on low, add the butter one piece at a time, until all are added. Then increase the speed to medium and beat until all of the butter has been incorporated, about one minute.
  5. Transfer the dough to a large greased bowl, and cover with plastic wrap. The dough is going to be sticky, use a spatula to scrape it into the bowl.
  6. Let it rise for 30 minutes.
  7. Place your fingers or a spatula underneath the dough and gently pull the dough up and fold it back over itself. Turn the bowl and repeat this folding again. Continue 6 to 8 more times, until all the dough has been folded over on itself. Re-cover the bowl with plastic and let rise for 30 minutes. Repeat this series of folding 3 more times, for a rise time of 2 hours and a total of 4 foldings.
  8. Tightly cover the dough once again and place in the refrigerator overnight (I left mine for two nights and it was fine).
  9. Remove the dough from the bowl and place it on a large floured surface.
  10. Knead the dough 10 to 12 times and then cover it with some flour and place a clean towel over top and let it come to room temperature. Grease a 9 x 13 baking pan.
  11. Melt the remaining two tablespoons of butter in a microwave safe bowl. In a separate small bowl, combine the sugar and cinnamon. Allow the butter to cool.
  12. Roll the dough into a 16 by 12-inch rectangle and brush the dough with the melted butter and sprinkle the cinnamon-sugar mixture evenly over the top, pressing it lightly into the butter so it adheres. Top with the chopped apples.
  13. Starting at a long side, roll the dough into a tight cylinder. Pinch the seam gently to seal it and position the dough seam side down. Use a sharp knife to cut the dough into 12-equal pieces. Transfer the rolls to the prepared pan. Cover the pan loosely with plastic wrap and let the dough rise until doubled, 1 to 1 1/2 hours.
  14. Make a batch of the date caramel sauce first. Soak your medjool dates in a bowl of just boiled water for about 10 minutes to soften them. Then remove from the water, cut them in half and pit them.
  15. Add the pitted dates to a blender along with all other caramel ingredients. Blend on high until smooth.
  16. Make the caramel icing: In a large bowl, combine the powdered sugar with the milk and vanilla and whisk well to combine. Add in half of the batch of the caramel sauce and mix to combine. Set this aside. You'll use the remaining caramel sauce on the cinnamon rolls later for serving.
  17. Preheat your oven to 350℉. Uncover the cinnamon rolls and place in your preheated oven to bake for 28-32 minutes, rotating halfway through. Place the pecans on a baking tray and bake on another rack at the same time for 10 to 12 minutes, until toasted.
  18. Transfer the baking dish to a cooling rack and let cool for five minutes, top with the pecans. Drizzle the caramel icing all over. Let them cool for another 10 minutes or so.
  19. Remove the rolls and serve with the extra reserved date caramel sauce on the side.