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.

Why You'll Love These Apple Pie Cinnamon Rolls:

• They're fluffy and super soft and pillowy
• You can make them in advance
• They freeze well
• You get apple pie flavor and a cinnamon roll all in one.
• They taste incredible

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.

Ingredients:

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.

• Eggs: you'll need 4 large eggs.
• Milk: any type will work here. I've used almond milk and it works the same as regular whole milk.
• Honey (or use maple syrup)
• Butter
• All Purpose Flour
• Active Dry Yeast (or instant)
• Brown Sugar
• Cinnamon
• Apples: you'll need about 2 cups of chopped apples. I like using honeycrisp.

For the Caramel Icing:

• Icing sugar/powdered sugar
• Milk
• Vanilla extract
• Dates
• Coconut milk
• Maple syrup

How to Make These Cinnamon Rolls with Apple Pie Filling

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).

Time to Assemble!

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.

Make the Icing

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.

How to Make The Date Caramel Sauce

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.

Bake Your Apple Cinnamon Rolls

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.

*drool*

Can I Make These Cinnamon Rolls Ahead of Time?

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:

• Prepare the rolls (roll out the dough, fill them, roll them up and cut them), and then put them in the prepared pan, without the rise time of 1 1/2 hours. Cover them loosely with plastic and refrigerate for up to 18 hours.
• When ready to bake, preheat the oven, and let the rolls sit at room temperature (with plastic wrap on) for about 30-45 minutes.
• Bake as directed.

Should I bake the Apples Ahead of Time?

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.

Substitutions:

Because of the nature of baking, I don't recommend many substitutions with this recipe.

• Refined sugar free: you can swap out the icing sugar for another type of sugar and grind it up. For example, you can use coconut sugar and grind it up first to create a powder. Then use that in the recipe as the powdered sugar. This will change the colour, but because we're making it a caramel icing sugar, it shouldn't matter. Obviously, the taste will change as well.
• Dairy-free: use a dairy-free milk such as oat or almond and try using a vegan butter (note- I haven't tested this with a vegan butter).
• Make a cream cheese frosting instead: I've also made a cream cheese frosting and skipped the caramel sauce on these and they're delicious.

There you have it, the best ever fluffy, soft and perfect apple pie cinnamon rolls.

Tips

• Give yourself enough time to make these: the folding technique makes such a difference in the end result, so please don't skip it.
• Make ahead of time: the dough can be made ahead of time and kept in the fridge for two days. When you remove it, follow the directions to knead 10-12 times and then let it come to room temperature.
• Use dental floss to cut the apple pie cinnamon rolls: personally I find this method the easiest for slicing the rolls.
• Add the butter to the stand mixer a little at a time: this allows the butter to better combine with the dough and makes for a very soft, puffy cinnamon roll!
• Use room temperature butter and eggs: yes, this makes a difference, so take them out ahead of time.
• Measure your ingredients correctly: nothing is worse than making a recipe only to taste it at the end and something is off. This is why I always recommend using a kitchen scale to weigh your ingredients, especially things like flour. If you don't have a kitchen scale, use the spoon and level method for measuring flour. The best way to measure flour is to fluff the flour first and then spoon it into your measuring cup and use the back of a knife to level off the flour (aka the spoon and level method). Do not scoop the flour directly into your measuring cup or pack the flour in and/or tap it to get more flour in. This will result in extra flour being used, which will make your baked goods too puffy, crumbly and/or dry.

Storage

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.

Other Baking Recipes to Try

• Gluten Free Savory Pumpkin Scones
• Vegan Tahini Chocolate Chunk Cookies
• Vegan Chocolate Chunk Banana Bread
• S'mores Cookie Bars
• Apple Crumble Bars
• Jammy Blueberry Bars
• Apple Stuffed French Toast
• Peach and Cherry Crisp

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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