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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I had some trouble forming the cookies and filling them the first time I tried this recipe, but I just finished a second batch that worked much better thanks to a little trick that I tried. I made the filling first and made little drops of it on a cookie sheet and popped them in the freezer until they got firm enough to use as filling without getting so messy! They do thaw quickly, but if you have a good pace, this is a pretty good way to make filling the cookies easier.
Made these with King Arthur gf flour. They were yummy!
For some reason, the filling kind of disappeared after I baked them. I had a similar problem with the inside out chocolate pumpkin cookies. Any ideas as to why that might be?
Hmmm… I’ve never had that problem. Maybe the gf flour absorbs the cream cheese?
I wanted to make these for weeks but I was so stressed, so all december long I had no christmas cookies. Now my best friend gave those to me together with the healthy poptart babies and… oh my! They’re perfect! Your blog is the best, Katie 🙂
I just bake some… they are quick, easy and delicious!!!! perfect for a 2 yo mom!!!! Thx
Didn’t see this post until today..but, I was with my son at the store just today and we thought rootbeer cookies sounded fantastic…and weird!
These cookies are PHENOMENAL!
Oh my goodness, Katie, they are like little dreamy sugar cookie pillows, and the filling is a lovely surprise in each cookie. Thank you so much for this recipe. It is the first one of many of yours that I have bookmarked, and they taste even better than they look! 🙂
Hi Katie, i was just thinking could I substitute the cream-cheese for chocolate?
just made these pillows today, they are heavenly and not too sweet!
I substituted apple sauce (3tbsp) for the oil and used 4tbsp skim milk. Delicious. I think I will try filling them with a mix of ricotta and strawberry next time!
Can you make a healthy version of “cookie butter”?
I can put it on my list of things to try 🙂
I just made these and they are utterly delicious, fluffy, light and oh-so-morish! I made them with whole wheat flour and it worked just fine. Thanks for the recipe!
Made these 3 days in a row for different parties/gatherings. Everyone absolutely LOVES them. I stuffed some with Nutella and others with peanut butter, and they are out of this world! You are a healthy baking genius.
Thank you so much for making them! I love your nutella idea :).
I’d love to try these! But I think I’d stuff them with vanilla icing instead of the vegan cream cheese. I didn’t even like cream cheese BEFORE I was vegan. 😛
Can the cream cheese stuffed pillows be made ahead and frozen?
Theses are good but makes like two cookies.
These look awesome and I can’t wait to make them! I just want to make sure I use the right amount of ingredients. You put 3/4 cup of flour but indicated 120g which is more like 1 full cup. 3/4 cup would be 90g according to my flour anyway. How much should I use?
Flours weigh different amounts depending on whether they are packed or not. If in doubt, it is always best to go with gram measurements in a recipe.
Love these! The dough was super easy to make and they don’t taste “healthy”. My 2.5 year old had such fun helping make them. Thank you for the recipe. I think it will end up being a favorite.