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Cinnamon Sugar Pillow Cookies

Soft and delightful cinnamon sugar pillow cookies – with a surprise filling!

Cinnamon Sugar Pillow Cookies

These pillow soft cookies are like:

A cinnamon roll

A sugar cookie

And a cream cheese danish… all in one cookie!

Also Try These Vegan Chocolate Chip Cookies 

sugar cookie stuffed with cream cheese
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It’s time for the holiday-cookie-season contest to commence.

The winner is the person who crams the most cookie-baking into this one short month.

Or really… the real winner is the one who eats the most cookies.

Chocolate Covered Katie Vegan Cookies

Today’s recipe is an updated version of a popular cookie recipe I first posted back in 2012.

This new 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!

cream cheese cookies
Cream Cheese Stuffed Cinnamon Sugar Pillow Cookies
cheesecake cookies
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If you haven’t started baking cookies this holiday season, why not begin today?

These light and fluffy homemade sugar cookies are always a big hit with both vegans and non-vegans, and they’re the perfect holiday cookie to give as a gift.

But if you do want to send them to others, I’d definitely recommend making extra so you can keep some for yourself!

Above – watch me make the cookies!

EASY CINNAMON SUGAR PILLOW COOKIES
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Cinnamon Sugar Pillow Cookies

Soft and delightful cinnamon sugar pillow cookies, with a surprise filling!
5/5 (3)
Total Time 11 minutes
Yield 15 – 20 cookies

Ingredients

  • 1 1/2 cup spelt, white, or oat flour
  • 3/4 tsp baking soda
  • 1/2 tsp baking powder
  • 1/2 tsp salt
  • 1/2 cup sugar, unrefined if desired, or xylitol
  • 6 tbsp oil or melted buttery spread (70g)
  • 1 1/2 tbsp milk of choice
  • 1 tsp pure vanilla extract
  • equal parts cinnamon + sugar or xylitol, if desired for coating
  • filling ingredients below

Instructions

  • For the filling (which you can omit if you want non-stuffed cookies), combine 4 tsp powdered sugar or Sugar-Free Powdered Sugar with 1/4 cup cream cheese (such as TJ's vegan), gently warmed or brought to room temperature so it's soft enough to stir or beat with the powdered sugar until smooth.
    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. 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 about 10 minutes on the baking tray and they will firm up as they cool.
    View Nutrition Facts

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More Holiday Cookie Recipes:

Vegan Peanut Butter Cookies

Vegan Peanut Butter Cookies

6 Ingredient Lemon Snowball Cookies

Lemon Meltaway Cookies

Keto Chocolate Chip Cookies

Keto Cookies

Oatmeal Peanut Butter Chocolate No Bake Cookies

Chocolate No Bake Cookies

Snowball cookies that literally MELT in your mouth.

Snowball Cookies  –  60 calories each

breakfast cookies

Breakfast Cookies – Super Healthy Recipe

fudge bars

Oatmeal Chocolate Fudge Bars

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More About The Cookbook

5/5 (3)

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Published on November 30, 2017

Meet Katie

Chocolate Covered Katie is one of the top 25 food websites in America, and Katie has been 
featured on The 
Today Show, CNN, 
Fox, The 
Huffington Post, and 
ABC's 5 O’Clock News. Her favorite food is chocolate, and she believes in eating dessert every single day!

Learn more about Katie

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Reader Interactions

222 Comments

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  1. McKenna S says

    I just put them in the fridge and i must say they kinda failed… They were dry and crumbly as dough even after adding almost 1/2 cup of oil and milk. I used regular white flour, whole lactose free milk, white sugar, and veggie oil. I’m sure they will still taste yummy, but im still confused and a bit disappointed:/

    • Kimberly says

      I think you used much too much milk. I know it sounds strange but your cookie’s texture was probably thrown off by too much liquid, not too little. The extra milk could make them gummy, I would think.

      • McKenna S. says

        That’s what I thought! But they were crumbly and almost powdery still. However, i baked them earlier and they came out absolutely delicious! Soft and “pillow-y”.

        • anonymous says

          Are you sure you measured the right amount of flour? 1 cup of liquid to 3/4 cup of flour wouldn’t be dry. It would be soup!

  2. amy says

    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!

      • Toni says

        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 🙂

        • Jill says

          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!

  3. Lauren says

    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!

  4. Andie says

    Yes!!! The holiday cookie posts have begun! Lol. I would definitely be in absolute ecstatic-ment if you could create an eggnog flavored cookie!

    • alloyjane says

      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.

      • Jane says

        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!! 🙂

  5. Jessica says

    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!

  6. Shawnee says

    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!(:

  7. Kimberly says

    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 :).

  8. Karla says

    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!

    • Brenda says

      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!

  9. Kari says

    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.

  10. laura says

    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

  11. Anonymous says

    chocolate rasberry, salted carmel or salted mocha/choxolate carmle, chocolate peppermint, eggnog, lemon, chocolate coconut or smores 🙂

  12. lil deli says

    you could do a chestnut chocolate cookie with flaked almonds and and powdered sugar to represent snow 🙂 but your pillow cookies look amazing!

  13. kel says

    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!

  14. ruby costa says

    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:

  15. Tina says

    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!!

  16. None says

    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.

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