I've been enjoying cinnamon rolls for Christmas morning for as long as I can remember. The tradition behind it made it something so special for me growing up that I decided to carry it on all these years later. So when I say I've tried a lot of cinnamon rolls, I've tried a lot. From the classic store bought Cinnabon, to making my own, it's been a journey to get them to come close to Cinnabon. I've tried making them healthier, with spelt flour, less sugar, grain-free (utter disaster) and vegan. No matter what, I couldn't quite nail it. So when I finally tried these, let me tell you, it was a very good day.
This recipe was originally published December 8, 2021 and has since been updated with more tips and photos.
Baking the perfect, soft and fluffy cinnamon roll isn't necessarily hard, but coming up with that recipe is. Which is why when I went on another quest to find the perfect cinnamon roll, I did some googling. I came across a recipe from Sarah Kieffer's website (The Vanilla Bean Blog). Her cookie pan banging technique is already so well known on Instagram (and beyond) and her cinnamon rolls are also a classic recipe that is consistently rated with 5 stars. I had high hopes for her rolls and they did not disappoint.
These cinnamon rolls with apple pie filling are a result of using her recipe and combining it with chopped apples and slathering a date caramel sauce all over. Usually I'm a classic cinnamon roll kinda girl, but the apples are a very nice addition here. So if you're on the fence about using them, I'd encourage you to try these delicious cinnamon rolls with apple pie filling for a change.
You don't need a lot of ingredients to make these cinnamon rolls with apple pie filling. And if you don't feel like making the date caramel sauce, you can easily swap that out for a classic glaze, or a cream cheese frosting.
For the Caramel Icing:
Making these apple stuffed cinnamon rolls is 100% worth the effort. Yes, it takes some time to prepare these, but most of the time is hands off. Also, how often do you make cinnamon rolls from scratch? Probably not often, so it's worth it when you do.
If you're using active dry yeast, you'll need to 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.
Once you can see that the yeast is foamy and alive, add the honey and eggs and mix.
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.
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.
Transfer the dough to a large greased bowl, and cover with plastic wrap. The dough is sticky, use a spatula to scrape it into the bowl.
Let it rise for 30 minutes and then follow the folding technique below.
This step of folding the dough over is part of Sarah's genius. As per Sarah, this helps to improve the structure of the dough and makes it easier to handle.
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. If you need to see a visual on how to do this, be sure to check that out over here.
Now, tightly cover the dough once again and place in the refrigerator overnight (I left mine for two nights and it was fine).
Remove the dough from the bowl and place it on a large floured surface.
Knead the dough about 10 to 12 times and then cover it with some flour and a tea towel and let it come to room temperature.
Grease a 9 x 13 baking pan (this is the exact one I use).
Melt the remaining butter in a microwave safe bowl. In a separate small bowl, combine the sugar and cinnamon.
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.
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 (or dental floss) to cut the dough into 12-equal pieces. Transfer the pieces to the prepared pan. Cover the pan loosely with plastic wrap and let the dough rise until doubled, 1 to 1 1/2 hours.
This is what they look like immediately after putting them away.
Here's what they'll look like after the second rise.
In a large bowl, combine the icing sugar with the milk and vanilla and whisk well to combine. Add in a half batch of the caramel sauce. Set this aside. You'll use the rest of the caramel sauce on the cinnamon rolls later.
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.
Add the pitted dates to a blender along with all other caramel ingredients. Blend on high until smooth.
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 for 10-12 minutes, until toasted
Transfer the baking dish to a cooling rack and let cool for five minutes, top with the pecans.
Drizzle the sauce all over. Let them cool for another 10 minutes or so.
Remove the rolls and top with the remaining date caramel.
Absolutely you can! I think it's way easier to split this up into two days personally. One night of kneading and then in the fridge overnight. Then all you need to do is knead them and let them come to room temperature, roll it out, fill them with apples and bake.
Also, you can make overnight apple pie cinnamon rolls as well. To do that, follow these steps:
No need to do this at all, they will soften in the rolls as they bake. Baking the apples ahead of time and then adding them to the rolls will also create too much liquid.
Because of the nature of baking, I don't recommend many substitutions with this recipe.
There you have it, the best ever fluffy, soft and perfect apple pie cinnamon rolls.
Obviously, these taste best when they're fresh, but they will hold up in the fridge and/or freezer.
Store these cinnamon rolls with apple pie filling in the fridge in an airtight container and eat them within a 3 to 5 days. When you want to enjoy one, microwave them for a minute or so (this tastes the best IMO).
You can also freeze apple pie cinnamon rolls (without any icing on them). Wrap in plastic wrap and place in the freezer for up to three months.
If you make these cinnamon rolls with apple pie filling, I'd love to hear from you. Feel free to tag me on Instagram, and/or leave a comment, rating or review below.
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The fluffiest cinnamon rolls with apple pie filling and a caramel drizzle. Perfect for Christmas morning!
This recipe was only slightly adapted from Sarah Kieffer's Cinnamon Rolls recipe found here.