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 made them GF using Bob’s Red Mill all purpose gf mix. I felt like i needed to add a little more milk, but the end product was super yum. yay!
Thanks for trying them with the gf mix! 🙂
Yes, I too made them with Bob’s Red Mill gf flour and my dough was also dry. I added a bit more milk, but I’m afraid not enough. I couldn’t get the dough to roll & didn’t get nearly as many cookies as you did (baked 2 minutes longer than you did); mine were just bigger but still SUPER DELICIOUS! Thank you 🙂
Same here – I used Bob’s Red Mill GF Flour and my dough resembled pie dough before you add the water. I added more oil (about 6 TBS total) and drizzled coconut milk in until the cookie dough began to gather itself. Then kneaded the dough together before I formed into balls. It was easy peasy – formed the dough into the balls for the cookies (about 20), then broke each ball into 1/2 pieces and squished flat, smeared some cream cheese onto one, crimped together, rolled back into a ball and rolled into cinnamon sugar. They cookies were eaten faster than they were made! Thanks, Katie!
Hi Katie,
I just made them and they are wonderful! I ate one as soon as the ten minute cooling period was up, and then I ate another. And I easily could’ve gone for a third :).
Thanks for the recipe, and happy holidays!
Yes!!! The holiday cookie posts have begun! Lol. I would definitely be in absolute ecstatic-ment if you could create an eggnog flavored cookie!
How about bacon cookies? My grandma used to make anise cookies. Cardamom?
Umm, CKK is a vegan blog…
But bacon bits are actually vegan! 🙂
oops my bad
Ooh but I’ve actually thought about chocolate-chip bacon cookies, using bacon bits (both Bacos and Fronteir are vegan) :).
These look absolutely delicious….making my mouth water, yum!
It’s not a cookie but Vegan Cream Puffs would be amazing!!!
Second this!
I second this. Vegan Cream Puffs! Because I haven’t had a cream puff in over a decade. Crazy cookie combinations? Uh… not sure if you’ve ever been out to Southern CA, but Native Foods used to have a rose cardamom cupcake but discontinued it on their new menu. So sad, but a rose cardamom cookie like this stuffed cookie would be awesome.
oh my goodness, YES PLEASE!! I’ve had plans to make a Christmas croquembouche this year, but four tries in, I still haven’t been able to get anything that resembles a cream puff!! Please, Katie, that would be the best Christmas present ever!! 🙂
CREAM PUFFS!!! Please make cream puffs.
Or gobs. Do you have any recipes for gobs? I really miss both of those things.
Ginger molasses cookies, candy cane cookies, lemon cookies, coffee cookies, and anything that’s fairly low in fat/sugar. I’m excited to try these and see what you come up with!
its not very crazy but i think red velvet crinkle cookies would be really fun for the holidays!
Omg these cookies remind me of sopapilla cheesecake! And for suggestions, mexican hot chocolate cookies, gingerbread, black and white cookies, lemon poppyseed, and chocolate with coconut butter filling!(:
Thank you! I have a Christmas cookie exchange coming up, and I wanted to bring a real winner, since I’m representing vegan cookies and people often think of vegan food as tasteless.
I did a test run of this recipe today, using the whole wheat pastry flour option, and they were out of the park! Exactly what I was looking for. I might take you up on your variation idea to try a peanut butter stuffing next :).
Katie, I have had (forgive me for this) an idea for a pumpkin/smoked brown sugar cookie! My sis in law gave me a bag of smoked brown sugar, and I haven’t done anything with it yet. It’s quite tasty!
Karla, you’re pumpkin/smoked brown sugar cookie sounds great, the smoked brown sugar is in the November issue of Sunset mag & they paired it with sweet potatoes…..so pumpkin sounds like a natural. Joyus made a peanut butter cookie with it, to die for! My husband is the mad genius who created the smoked brown sugar, so I can vouch for it’s cookie compatability!
Looks sooo good!
How bout red velvet cookies with creamcheese butter mint frosting (like those melt in your mouth pastel mints). Or dark chocolate cookies with red velvet frosting! Ooo that’d be pretty. I second the eggnog hot chocolate cookies, or eggnog coffee cookies, or eggnog gingerbread, red velvet with egg nog frosting… I’d better stop.
yum these are awesome! I used galaxy cream cheese.
Oh Katie these look amaaazing! You’re killing me!
chocolate-chocolate-chip biscottis, something chocolate-y and orange-y,
and I second cream puffs!
thanks!