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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These look awesome and I can’t wait to try them Katie!
For cookie flavors how about Fruit Cake, Stuffed Cornbread, or Chocolate Lemon?
This isn’t a crazy flavor but I want fresh baked gingerbread cookies for the holidays!
I second this!
And third it, fourth it, fifth it… into infinity!
But I also think rainbow cookies, monkey-bread cookies (is that a cookie flavor? Or did I just combine two desserts? Well, it’d be an interesting experiment), peanut butter-with-jelly cookies… or maybe even… pumpkin and gingerbread combined into one cookie? (The latter would make my life complete. I could die happy with that… especially if it was an oatmeal cookie to boot.)
YAY! Cookie season!
I have recently loved pouring So Delicious coconut milk eggnog into my hot cocoa. How about Chocolate Eggnog Cookies??
YES PLEASE!
I also want to ask in a separate comment; for Christmas every year we go up North (or at least, farther North) to visit my mom’s extended family, several members of which are diabetic and could use a healthier/lower sugar option for desserts, since the typical dessert there consists of super-decadent cupcakes, huge cream puffs, pineapple cheesecake… you get the picture. (I could use healthier options too, since I can easily go through 20 units of any dessert item in a sitting… it’s a miracle I’m not morbidly obese yet). Do you have any recommendations?
I really don’t know much about what’s acceptable and what’s not on a Diabetic diet, so it’d be irresponsible of me to give recommendations… but would today’s recipe work if you used the xylitol option? Here is a link to all my cookie recipes: https://lett-trim.today/chocolate-covered-recipes/healthy-cookie-recipes/%3C/a%3E%3Cbr /> Maybe ask your relatives what’s acceptable on their specific diets, then see if any of the cookies are a match (especially if you use the xylitol options).
I can say as a Type 1/insulin dependent diabetic that all of Katie’s recipes I’ve tried (which is a lot of them) have worked fine for me and I use the real sugar. As for carbohydrates I think it varies by person and you can’t put all diabetics in a box. I average 250 grams a day which is not low carb. I exercise daily and average less than 18 units of insulin via an insulin pump which is a very small amount considering I don’t produce any of my own. I would take Katie’s suggestion and ask the people to see what they’re dietary needs are because everyone is different. Another point I’d like to make is that recipes with more healthful ingredients that do contain real sugar don’t spike the blood sugar like ones with a lot junk. So the source of the carbs makes a difference too.
i know diabetics, have to avoid lots of carbs, so of course a sugar free substitute would be needed for whatever you make. if you use one that measures like sugar you can do any recipe and just switch it for the sugar. If you use stevia but not the baking kind there are still lots of recipes around that use the packets/stronger kind. (this site uses those in a lot of recipes) Another thing you could try is almond flour. There is carbs in it, but its super low. there are lots of recipes you can make with it, or even sub it in for regular flour in some recipes.
My husband (type II Diabetic) has blood sugar spikes from wheat, even whole wheat. Apparently this is not unusual. Wheat seems to affect him as much as sugar does.
Its funny that you mention that. I just saw a dr oz yesterday that did a test about that…some dr was on stating that even whole wheat causes problems and can spike your sugar worse than a candy bar. Dr oz tested it out on 5 people and it was true for 3 out of the 5 people. Whole wheat bread actually spiked twice as bad as a whole chocolate bar.
I believe he was referring to Dr. Davis of “Wheat Belly” fame. We’d already figured it out with dh, but hearing that this is really common just made me mad. Kind shoots “healthy whole grains” in the foot.
They look so soft and delicious – just the way I like it! Awesome! I’ll have to make my own cream cheese again and then I will try this recipe! =)
chocolate chili lentil and garbanzo bean cookies (chocolate chili cookies for short).
dang, I just read the other chocolate chili suggestion…
ok, here is another: sweet potato cranberry cookies
chocolate chili lentil and garbanzo bean cookies
sweet potato cranberry cookies
chestnut and apple cookies (using chestnut flour)
chai cookies using all coconut products (flour, oil, shredded, extract, sugar, water/milk)
Mmmm!! I’ll have to experiment with the gluten-free, sugar-free option for this. Please make some gluten free cookies for us Celiac and gluten intolerant/ allergic people, please and thank you 😀 What about Almond-Orange-Chocolate Cookies, Chocolate Cherry Almond Cookies, Salted-Caramel Chocolate Cookies, Lemon Pistachio Cookies, or Green Tea Lime Shortbread. Oh the possibilities!!
Mmm those are great ideas!! Yumm!! 😀 I hope Katie sees these haha! 😛
Mmm those look delicious! Chocolate chili sound great (but please without lentils like other people have commented!) And chocolate crinkles sound good too! Here are some other ideas: Apple Cider, Eggnogg, Peppermint Chocolate Chip, Sugar Plum, Gingerbread, M&Ms, Red Velvet, and the Jelly Bean one sounds awesome too! I am SOOO excited for holiday cookies I CANNOT wait!! 😀
Also maybe like something that has to do with red and green? 🙂 And I know this would probably be super hard but I LOVE gumdrops so maybe you could make those? It would be so cool! 😀
How about chocolate with bacon bits cookies?
Or Fak’in bits as Katie is Vegan!
I think you should really tackle a chocolate-chili cookie. I love that flavor of chocolate bar, but never had it in a cookie. It would be sure to be good if you designed it.
Happy cookie season!
hmmmm….penut butter sugar cookie, candy-cane chocolate chip, ginger snap and white chocolat, dulce de leche (sp?) sugar cookie, tiramisu, carmel coffee peanut butter, red velvet chocolate swirl, peanut butter white chocolate, coconut red velvet, butterscotch ginger snap
Haha I already sent all my brainstorming ideas on twitter, hope you find some good ones!
those look amazing! i love the yummy center!
This looks so yummy!