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
Snowball Cookies – 60 calories each
Breakfast Cookies – Super Healthy Recipe
These are so SO good! I was out of both coconut and vegetable oil, so I wound up subbing in butter instead (obviously won’t work for vegans), and they still turned out amazing! I also mixed in some mini chocolate chips in the cream cheese filling, because just about everything is made more delicious with chocolate chips. I highly, highly recommend—these are definitely going to be a staple of my Christmas cookie making 🙂
I could go for some chai tea cookies 8) or maybe some lavender cookies (these sound gross, but lavender icing is actually REALLY yummy! It’s not too perfumey or overpowering) Other ideas:
-oreo mint (not very creative, but sounds good lol)
-maybe something fruity like strawberry-kiwi or cherry-lime, OR cranberry-orange!!!
-vanilla-coffee? -this is weird, but it might be good
-popcorn, actually I think kettlecorn cookies would be better, the sweet and salty thing
-marshmellow/chocolate
I hope you love these ideas, CCK! I adore your blog soooo much! Thanks for sparking my interest in blog-following! I have to ask, is it difficult to get a blog started and to get followers? I am interested in starting one, but don’t really know where to start! Thanks (:
OH YES.
KETTLECORN.
Also, with the vanilla coffee: yum! Maybe you could do a coupple different types of coffee inspired cookies, like latte/expresseo/cappuchino cookies. Or black coffe cookies swirled with cream and sugar cookie dough!
ERMAHGHERD.
BLACK COFFEE COOKIE DOUGH. SWIRLED WITH CREAM AND SUGAR COOKIE DOUGH. IT IS COFFEE WITH SUGAR AND CREAM. ER. MAH. GHERD.
I’d better stop now. 😉
Wow, that is inspired, the coffee/cream cookie. And a kettle corn cookie, I could get behind that.
Thanks for all the ideas!
Yeah, it takes a few years… I’ve been blogging for a long time, and for the first year I think I had maybe 5-10 readers ;).
I love that you titled these pillow cookies! If I used these as pillows though, I can assure you that not only would it be really messy but these would be gone in a heartbeat.
You should make a green cookie by adding spinach to sugar cookies and then add pistachios and and craisins for the holiday flavors and white chocolate chips for sweetness.
cookie suggestion – I have been making this habanero jelly recipe and it is sooooo good
http://www.themeaningofpie.com/2011/07/habanero-jelly-2/
I plan to try it as a thumbprint cookie using the pepper jelly! What do you think?
can’t wait to try these. they look yummy!
Hmm. Soda flavors
A bit unusual, I know, but I think it’d be an interesting idea to at least try out
Root beer extract
Cherry extract
Orange extract
etc.
I just made these gluten free by substituting 3/4 cup sorghum flour plus 1/4 teaspoon xanthan gum for the flour. Used 2 Tablespoons of plain unsweetened soy milk ( I find most gf flours are drier than wheat flour). Otherwise followed your recipe. The dough was soft and a little crumbly. I got 18 small balls of dough, flattened them and added the cream cheese filling, they did not roll into a ball very well so I pinched the edges together as well as I could and sprinkled the cookies with the cinnamon sugar. Baked for 15 minutes ( at an altitude of 5 thousand feet most things take longer to bake here). A couple are very crackled on top with the filling showing through, so had to eat the worst looking one. Very tasty and worth the trouble of forming them. Thanks for the recipe.
These look amazing as usual. I get excited about cookies. You could be inspired by crazy macaron flavours and transfer them to a cookie. I read an old post on rasberricupcakes.com the other day where she tried about 50 different flavours and some of them sounded incredible. Avocado, burnt toast and butter, truffle.
I love an indian dessert called Gulab Jamun. I would love a cookie that reminded me of that taste. I think it has rosewater and honey.
I cant think of an Indian dessert that I have ever NOT loved. I might very well need to try this guy- anything with rosewater always tastes perfumey and yummy 🙂 Have you ever tried gajar ka halwa? I had it once before I was vegan, and it was amazeballs. 😀
I would love a cookie with the same sort of banana chai flavour as a drink you did, I can’t remember what it was called but it had the chai spices, a frozen banana and milk of choice from memory.
Another cookie flavour I would like is a fruit mince pie flavour, the dried fruits, the stewed apple, a touch of citrus peel, the spices, yum.
These sound great, am definitely giving them a go once I have all the bits.
Ah, the Chai-Nana Shake! That one is definitely yummy. 🙂
Chocolate orange, Chocolate oranges are a traditional Christmas gift in my family.
Chocolate Salted Caramel Pretzel (this isn’t creative, but I don’t remember seeing a recipe for it)
Chocolate covered cranberry, I made muffins with a can of cranberry sauce once, they turned out really moist and delicious.
This isn’t a flavor but.. Waffle cookies! I’ve heard you can make cookies in a regular waffle iron! Just some ideas.
I LOVE your blog! Especially the oatmeal recipes 🙂 Recently I have been craving cinnamon buns…how about a healthy cinnamon bun recipe? 🙂
Going in the cookbook… but I’m pretty sure I will post it on the blog as well, as soon as I’m allowed!
Candy Cane cookies? Fruit cake cookies? Rum and Raisin? Pudding-type cookies?These look yum by the way!
Definitely want to see your version of the potato chip & chocolate cookie. Can’t see how that could possibly be made healthy, but could be worth a shot 🙂
-Gab
These were yum
But I was wondering if u know a recipe that is sugar free for meringue or French macaroons
I don’t, but it is on my to-do list!