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
Notes
Have you made this recipe?
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Becky says
OMG! I need to make these tonight . They look so delicious.
Paige Flamm says
These cookies lookl so fun!
Paige
Nicole @ Bento Momentos says
These look AMAZING!
Cassie Autumn Tran says
How yummy! These look like the skinny snickerdoodles and the stuffed sugar Nutella cookies! I never would have thought of stuffing cream cheese in a cookie–what a clever idea!
Cooker says
What is the cream cheese alternative? :-l
Jason Sanford says
Do you mean, what can you replace cream cheese with? You actually don’t have to fill them at all. They are quite delicious without the stuffing too.
Jeri says
They look and sound delicious. Was wondering approximately how much dough is used for each ball or the size of each ball, whichever. Thanks…
Cinnamon Zone says
These are great as they have this surprise filling inside which I am sure no one will expect. The cookies look really moist and soft in texture and the filling is such a simple one with no fuss involved but nevertheless a great addition.
Amanda M Heath says
What if I used self rising flour, would it work? I know it does just great for some of the recipes that call for straight flour, some it ruins. If it will work, do I add any baking powder, or baking soda at all, if so in what combination? I don’t have any baking soda at the moment is my problem. Thanks for any info from anyone. I would just experiment, but I’m low on ingredients and money, and hate wasting anyway.
Danielle Morgan says
Can this be mixed in a food processor?
Jason Sanford says
We haven’t tried it so honestly can’t say! Be sure to report back if you try!
Jason (media relations)
Laurie Johnson says
Do these cookies freeze well? I’m looking for healthier cookie recipes for my church’s coffee hour. I’d make a larger batch if they will keep from one week to the next. but the filling has me wondering.
Jason Sanford says
I’m not sure about the filling, but you could always omit the filling and the cookie part definitely freezes well! Then they’re like snickerdoodles 🙂
Jason
Tara says
I just finished making the dough and fingers crossed they bake well tomorrow!
Man these were a little difficult to make, but it might be because I doubled the recipe. I think it would have been better if the filling was like the recipe I copied below. ??♀️
https://sallysbakingaddicton.com/cream-cheese-stuffed-red-velvet-cookies/
Kallie Rinker says
OMG! Luv those cookies!
Jennifer Bowen says
Can you make these without the chilling time?
Steve Watson says
I would love to eat these cookies but I’ve diabetes 🙁
Katie says
I mean you still can but it’s a lot to dose for. Or you can change the flour to almond flour and use almond milk rather than regular milk and use a sweetener rather than sugar. Y’know cut most of the carbs out and they should still taste pretty good. I have to make food for my fiancé and he’s diabetic so I kind of have an idea how to make these with less carbs
Janis says
I tried making this recipe twice and each time, the cream cheese center baked into the rest of the cookie. Still tasted amazing, but no surprise gooey, creamy center 🙁 Anyone know what I’m doing wrong? I followed the recipe to a T each time. The second time, I even refrigerated the cream cheese mixture for a while thinking it may not melt as fast. The first time, I used Kite Hill’s almond cream cheese, the second time I used Miyoko’s.
Suzanne says
This looks delicious, thank you sharing!
Linda Sue says
Do the nutrition facts include the cream cheese filling? Thank you for the recipe, I’m about to put my first batch in the oven and I’m super excited to see how they turn out!
CCK Media Team says
They do indeed 🙂
Katie says
These were a little more difficult to make than I was led to believe, but absolutely worth the effort. At first, I had trouble getting the dough to stick to gather and found them impossible to roll into a ball with the filling in them. The best I could do was gently pat the 2 parts back together. But so delicious!
Lulu says
I was hoping these wouldn’t be good because they took a little extra effort. But OH MY! These are so good. A keeper. Worth the effort.
It would be great to add some info about storing. I want to give some to a friend in 5 days and I don’t know if I should refrigerate, freeze, or leave out well covered. I am thinking I’ll refrigerate.