Cinnamon sugar pillow cookies are soft and delightful holiday cookies, with a surprise cream cheese filling hidden inside!
Fluffy cinnamon sugar pillow cookies
These pillow soft cookies are like a cinnamon roll, a sugar cookie, and a cream cheese Danish all in one incredibly delicious cookie.
Each year around Christmas, they are always one of the first cookies to disappear on the holiday cookie tray, and for very good reason.
If you haven’t started baking cookies this holiday season, why not begin today?
One pillowy bite, and you will fall in love.
Also try these Vegan Chocolate Chip Cookies
The best pillow sugar cookies
Today’s recipe is an update of an incredibly popular sugar cookie recipe I first posted all the way back in 2012.
This new and improved version of the recipe is easier to follow and makes a bigger batch, because you will definitely want more of these cookies once you try them!
They are hands down the best stuffed sugar cookies you will ever taste.
The light and fluffy homemade cookies are always a big hit with both vegans and non vegans, and they are the perfect holiday cookie to give as a gift.
But if you do want to send them to others, I definitely recommend making extra so you can keep a few for yourself.
Use leftover cream cheese for this Oreo Fluff Recipe
Cinnamon sugar pillow cookie recipe video
Above, watch the step by step video
Ingredients for the recipe
The cookie base calls for flour, sugar, baking soda, baking powder, salt, oil or butter, water, and pure vanilla extract.
You will need equal parts ground cinnamon and sugar for the optional coating. The cheesecake filling ingredients are simply powdered sugar and cream cheese.
Flour – Spelt flour is my preference here. It is a healthy, whole grain alternative to white flour yet yields a lighter texture than whole wheat flour. All purpose flour, oat flour, and some brands of gluten free flour also work.
Sugar – This can be traditional white sugar, unrefined coconut sugar, or granulated xylitol for sugar free cookies. I have not tried pure maple syrup or honey so cannot recommend either of those options as substitutions.
Cream Cheese – Dairy cream cheese and nondairy cream cheese work equally well in these cookies. As a fun alternative, you can stuff the cookies with something entirely different, such as crunchy peanut butter or Homemade Nutella.
Butter – Look for salted or unsalted butter at the grocery store. For vegan pillow cookies, go with a full fat plant based alternative. Or substitute melted coconut oil or vegetable oil for crispier sugar cookies without butter.
Vanilla Extract – Buy pure vanilla extract for the best results. Imitation vanilla flavor is less expensive but will impart an artificial aftertaste that you do not want.
How to make the cookies
Start by gathering all of your base and filling ingredients.
For the optional filling: Let the cream cheese come to room temperature so it will be easier to blend smoothly.
Add the powdered sugar to the softened cream cheese, and beat in a stand mixer or with hand beaters. If you do not own either of these, you can also patiently whip it together by hand until thick and smooth.
Set the filling aside while you make the sugar cookies.
For the cookies: Combine the flour, baking soda, baking powder, salt, and sugar in a large mixing bowl. Stir well, then add in the melted butter or oil, water, and vanilla extract to form a sugar cookie dough.
If the dough is too dry for some reason (climate, humidity, elevation, etc.), very slowly add a little more water or oil.
Use your hands to smush the cookie dough into one giant ball. Or use my less messy trick of transferring the mixture to a large Ziploc bag and smushing it into a ball from inside the bag.
Break off large cookie sized amounts, and roll into balls.
If filling the cookies, break each ball in half. Add about a half teaspoon of cream cheese filling to one half, then place the other piece of dough on top and roll back into a ball.
For soft, chewy cookies, chill the unbaked cookie dough balls for at least thirty minutes or until cold to the touch. You may skip this step if in a rush.
Preheat the oven to 325 degrees Fahrenheit.
Roll the balls in cinnamon sugar and place them on a cookie baking tray.
Bake on the center rack of the preheated oven for eleven minutes. The cookies should look underdone when you take them out of the oven.
Let cool before handling, during which time they will firm up considerably.
Pillow cookie storage tips
Once cooled, transfer cookies to a serving tray or container.
Store leftover cookies in an airtight container for up to five days on the counter. Or freeze leftovers in a covered container for up to about three months.
If you like soft pillow cookies, go with a plastic container. For chewy cookies with a slightly crispy texture, store them in a glass container.
Cinnamon Sugar Pillow Cookies
Ingredients
Pillow Cookies
- 1 1/2 cup flour (spelt, white, or oat)
- 3/4 tsp baking soda
- 1/2 tsp baking powder
- 1/2 tsp salt
- 1/2 cup sugar (or coconut sugar or xylitol)
- 6 tbsp oil or butter
- 1 1/2 tbsp milk of choice
- 1 tsp pure vanilla extract
Cream Cheese Filling (optional)
- 1/4 cup cream cheese or vegan cream cheese
- 1 1/2 tbsp powdered sugar or sugar free powdered sugar
- equal parts cinnamon and sugar or xylitol if desired for coating
Instructions
- In a mixing bowl, combine first five ingredients, and stir well. Stir in the oil, milk, and vanilla to form a cookie dough. Only add extra milk if it's still too dry after a full minute of stirring. (I've never had to add more than the 1 1/2 tbsp milk.) Smush into a giant ball with your hands, or transfer dough to a plastic bag and smush into a ball once the dough is inside the bag. Now roll into balls. Break balls in half, flatten each half a bit and add a little filling to one half, then place the other half on top and re-roll. For softer cookies, chill 30 minutes or up to a day. Preheat oven to 325 F. Roll balls in cinnamon sugar, place on a baking tray, and bake on the center rack 11 minutes. They'll look underdone when you take them out, so let them cool fully on the baking tray and they will firm up as they cool.View Nutrition Facts
Video
Notes
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one question – why do you include both baking powder and baking soda? aren’t they the same thing?
and for cookies, can you make a healthier version of those stained-glass-window cookies that are so much fun at christmas time? I would love that! (in case you don’t know what i’m talking about, here’s a link) http://www.simplyrecipes.com/recipes/stained_glass_cookies/
Baking soda and baking powder are different, but the difference is minimal. Soda needs to be combined with something acidic when baking to make the baked good rise. Powder already has that acidic ingredient in it (cream of tartar). Baking soda is purely sodium bicarbonate, but baking powder has cream of tartar and (usually) cornstarch. There’s also the difference if single and double acting baking powder which I won’t get into. Hope that explains it!
Yummy! What original cookies! How about red hot orange cookies? Or peanut butter molasses cookies.
This is a very creative idea!
How about a smore cookie? Have you tackled that one yet??
Yes! I want a smore’s cookie!
I sometimes make whole wheat rosemary cookies…a friend asked me to come up with a recipe for her open house and I did those for years. In essence, it is a whole wheat sugar cookie with fresh chopped rosemary in it.
black licorice/anise cookies, some kind of cookies with dried figs, chocolate orange cookies
I started a blog (largely because of awesome, inspirational bloggers like you that I obsessively read) and I linked you in my about page! (I hope that’s ok) 🙂 See!
http://ejsediblejoys.wordpress.com/about/
Thank you so much… good luck with your new blog. It looks great so far!
My chocolate chocolate-chip cayenne cookies are to die for!!
I used to work at Starbucks and for a while we had a “London Fog Latte” which was Earl Gray tea, vanilla, and steamed milk. I always made mine with soy milk SO GOOD. I think those flavors would make a good cookie. A tea cookie with the tea already inside it! 🙂
That sounds SO good! Do you know if you can still get that at Starbucks? And I agree, sounds like it would make a great cookie.
Any decent coffee house (Starbucks included) should know what a “London Fog” is if you request it. When I was a barista I would occasionally make my own version with yerba mate, coconut syrup, vanilla syrup and steamed milk of choice. I called that one a “Rainforest Mist” playing off the “London Fog”, but I don’t think any other barista will have heard of it!
Something with chocolate and orange, or cloves and orange…or chocolate, cloves, and orange!
Oh. My. Yummmmm! CANNOT wait to make these and try them!!!!
Something oil-free
These look so yummy! I’ve been dying to start my Christmas baking but I haven’t been able to because my husband and I just moved to Texas and we have yet to get settled into our new place. Hotel rooms aren’t exactly conducive to baking… Hopefully I’ll be able to make some of your delicious treats soon!
katie. this has gotten rough. I am finding new recipes on here before they are tweeted, and typically before any of my homework has been done. I have finals this week and you are only encouraging mt procrastination by coming up with these crazy recipes. Obviously this is not your fault…. but you’re younger audience is having a rough time ignoring you during these last few weeks. I’m pretty sure I’m not alone.
You’re not alone! I spend way too much time reading this blog and daydreaming about every dessert and baking the desserts, rather than doing my hw (;
I would love to try a chocolate chili cookie!! That sounds like it could be really great! Doooo it!!
I just put them in the fridge and i must say they kinda failed… They were dry and crumbly as dough even after adding almost 1/2 cup of oil and milk. I used regular white flour, whole lactose free milk, white sugar, and veggie oil. I’m sure they will still taste yummy, but im still confused and a bit disappointed:/
I think you used much too much milk. I know it sounds strange but your cookie’s texture was probably thrown off by too much liquid, not too little. The extra milk could make them gummy, I would think.
That’s what I thought! But they were crumbly and almost powdery still. However, i baked them earlier and they came out absolutely delicious! Soft and “pillow-y”.
Are you sure you measured the right amount of flour? 1 cup of liquid to 3/4 cup of flour wouldn’t be dry. It would be soup!
Same here.:(