Sign up for NEW free healthy recipes - Currently over 300,000 subscribers!

Cinnamon Sugar Pillow Cookies

Pin It!

It’s time for the holiday-cookie-season contest to commence.

Cream Cheese Stuffed Cinnamon Sugar Pillow Cookies

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!

These are fantastic!!! Like eating a cinnamon roll, a sugar cookie, and a cream cheese danish... all in the same cookie! @choccoveredkt

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!

cream cheese cookies

If you haven’t started baking cookies this holiday season, why not begin today?

Make up a batch of these pillow-soft sugar cookies to start the holidays off on the right Christmas-stockinged foot. (Or Hanukkah-stockinged, Kwanzaa-stockinged, etc.)

One of my favorite holiday cookie recipes - it's like eating a cinnamon roll, a sugar cookie, and a cream cheese danish... all in the same recipe @choccoveredkt


Cinnamon Sugar Pillow Cookies

(makes 11-13 stuffed cookies)

  • 3/4 cup loosely packed spelt, white, or ww pastry flour – Readers say you can use a gf all-purpose if you add extra liquid so it’s not crumbly (120g)
  • 1/4 tsp baking powder
  • 1/4 tsp salt
  • 1/4 tsp plus 1/8 tsp baking soda
  • 1/4 cup sugar or xylitol (55g)
  • 1/2 tsp pure vanilla extract
  • 2-4 tsp milk of choice (8-16g)
  • 3 tbsp coconut or vegetable oil (35g)
  • a bowl of equal parts cinnamon and sugar or xylitol for rolling – Omit if desired
  • filling ingredients listed below

For the filling (which you can omit completely if you want regular, non-stuffed cookies): combine 2 tsp powdered sugar or Sugar-Free Powdered Sugar with 2 tablespoons cream cheese-style spread (I used Tofutti non-hydrogenated, but I’m sure other full-fat brands such as Follow Your Heart or Trader Joes would be fine.) Beat well, then set aside.

In a mixing bowl, combine first five ingredients and stir very well. In a separate bowl, combine all liquid ingredients and stir. Pour wet into dry and stir to form a cookie dough. Smush into a giant ball with your hands (or, as an easier trick: transfer dough to a plastic bag and smush into a ball once the dough is inside the bag). Now roll into 22-26 mini cookie dough balls, then flatten each and divide the filling among only half of the flat discs. Place the other discs on top, cinch the sides, then roll into balls. Roll the balls in the bowl of cinnamon-sugar, place on a baking tray, and chill for at least 30 minutes. (If you desire crispy cookies, you can skip this chilling step.) Preheat oven to 325, and cook 11 minutes- they’ll still look a little underdone, but that’s okay. Important: allow cookies to cool at least 10 minutes before trying to remove from tray. For step-by-step photos, substitution notes, and troubleshooting, see the nutrition link below:

View Pillow Cookies Nutrition Facts

cheesecake cookies

Link Of The Day:

healthy chocolate chip cookies

Healthy Chocolate Chip Cookies

Rate this recipe

Katie is the baker, photographer, and author of the popular blog Chocolate-Covered Katie. Her favorite food is chocolate, and she believes in eating a balanced diet that includes dessert every single day. More about Katie—> 
Tags: , , ,

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Heidi Lynn says:

    These look awesome and I can’t wait to try them Katie!
    For cookie flavors how about Fruit Cake, Stuffed Cornbread, or Chocolate Lemon?

  2. Suzanne says:

    This isn’t a crazy flavor but I want fresh baked gingerbread cookies for the holidays!

    1. carolyn says:

      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.)

  3. Samantha says:

    YAY! Cookie season!
    I have recently loved pouring So Delicious coconut milk eggnog into my hot cocoa. How about Chocolate Eggnog Cookies??

    1. Krystal says:


  4. carolyn says:

    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?

    1. CCK says:

      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:
      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).

      1. Heidi Lynn says:

        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.

    2. Tiffany H says:

      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.

    3. JP says:

      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.

      1. Tiffany H says:

        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.

        1. JP says:

          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.

  5. 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! =)

  6. Dara says:

    chocolate chili lentil and garbanzo bean cookies (chocolate chili cookies for short).

  7. Dara says:

    dang, I just read the other chocolate chili suggestion…
    ok, here is another: sweet potato cranberry cookies

  8. Dara says:

    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)

  9. Alysha says:

    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!!

    1. Julia says:

      Mmm those are great ideas!! Yumm!! 😀 I hope Katie sees these haha! 😛

  10. Julia says:

    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!! 😀

    1. Julia Smith says:

      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! 😀

  11. Irene says:

    How about chocolate with bacon bits cookies?

    1. Kristall says:

      Or Fak’in bits as Katie is Vegan!

  12. 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!

  13. Stephanie says:

    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

  14. Haha I already sent all my brainstorming ideas on twitter, hope you find some good ones!

  15. those look amazing! i love the yummy center!

  16. Michelle says:

    This looks so yummy!

  17. Shani says:

    one question – why do you include both baking powder and baking soda? aren’t they the same thing?
    and for cookies, can you make a healthier version of those stained-glass-window cookies that are so much fun at christmas time? I would love that! (in case you don’t know what i’m talking about, here’s a link)

    1. Baking soda and baking powder are different, but the difference is minimal. Soda needs to be combined with something acidic when baking to make the baked good rise. Powder already has that acidic ingredient in it (cream of tartar). Baking soda is purely sodium bicarbonate, but baking powder has cream of tartar and (usually) cornstarch. There’s also the difference if single and double acting baking powder which I won’t get into. Hope that explains it!

  18. Yummy! What original cookies! How about red hot orange cookies? Or peanut butter molasses cookies.

  19. krista says:

    How about a smore cookie? Have you tackled that one yet??

    1. laura says:

      Yes! I want a smore’s cookie!