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
Reader Favorite Holiday Cookie Recipes
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Breakfast Cookies – Super Healthy Recipe
1. something that combines rice krispies maple syrup and peanut butter (Us Canucks love our maple syrup!)
2. I am making a vegan chocolate dip for fruit for a potluck on Monday, easiest ingredients ever- coconut milk, avocados (Can’t remember if you mentioned you hate avocados??) and good quality melted dairy-free dark chocolate, something that uses these ingredients maybe as a frosting for cookies would also be good!
3. some sort of grain free cookie that incorporates bananas coconut oil and cocoa powder
I already said this on Twitter but green tea cookies! (with red bean or white chocolate or even milk chocolate would be soooo good)
chocolate rasberry, salted carmel or salted mocha/choxolate carmle, chocolate peppermint, eggnog, lemon, chocolate coconut or smores 🙂
you could do a chestnut chocolate cookie with flaked almonds and and powdered sugar to represent snow 🙂 but your pillow cookies look amazing!
I don’t know how you’d do it, but what about something with a pine scent to it? Maybe a citrus-pine mix…
White chocolate chai cardamom would be interesting….or a spicy hot pepper inspired chocolate cookie! I just made almond pillow cookies last night btw! Inspired by the fresh Market!
i have a chai cookie recipe that i’ve been working on that’s pretty good. i don’t often see chai&chocolate paired together (maybe for good reason) but that might be something fun to explore c:
These look yummy Katie! I’m super excited for cookie baking season! 🙂
These look sooo good!! Might have to try making these… Thanks! 🙂
I made these using Jukes Gluten free flour, worked well, but quite dry and crumbly. I had to add more milk, probably about a tablespoon more, could have used a bit more, but still very yummy.
I would love to see you come up with a chocolate pomegranate cookie! We love pomegranate!!
Wow. As usual, these look amazing!!
I absolutely love /all/ of your recipes. I recently tried the Lentil Sloppy Joe and it has become a family favourite, even with my father, a hardcore meat eater. I’ve been vegan for three years now, and no one’s recipes interest my more than yours. I adore this recipe, and I’m going to save this weekend just for it.
I reckon it would be nice to have this recipe with a mix of mint and chocolate. I always feel like peppermint around Christmas time.
Healthy gingerbread? I know it’s pretty typical, but I haven’t found any great healthier versions of it anywhere…
or HEALTHY NANAIMO BARS! I know you can do it!
Have you ever seen the dark chocolate orange in orange raping like at trader joes? Well dark chocolate orange cookie!!! You chop up the chocolate orange and add to your cookie dough!!
I cannot get over how brilliant these are! While I’m not a big cream cheese lover myself, I would most definitely bring them to a party. Heck, vegan cream cheese probably grosses me out quite a bit less (do you even want to know how cheese gets that texture? ew, no), I might even found a new cookie that I love.
As for unusual cookies, Christmas makes me think of things like cranberries, peppermint, eggnog, chocolate, oranges…maybe a fruity/minty cookie? That doesn’t sound too bad… Looking forward to the rest of your holiday recipes!
Soft maple cookies with bits of bacon
This sounds awesome! Maple and Bacon make a great combination.
And the best part is Bacon Bits are often vegan!