Cinnamon Sugar Pillow Cookies

Cinnamon sugar cookies with a deliciously sweet surprise in the middle!

We’ve done our fair share of decadent desserts here on 12 Tomatoes. Everything from S’mores Brownie Pudding Cake to Chocolate Cheesecake Lasagna, and pretty much everything in between, but sometimes it’s nice to get back to the simple things. Like sugar cookies, for example.

These Cinnamon Sugar Pillow Cookies take a basic sugar cookie recipe and dress it up a bit – but not too much. We’re still keeping things pretty simple, though I think you’ll like the hidden surprise these cookies pack…

You might be wondering what makes these “pillow” cookies. Well, as you can see, they are certainly softer and puffier than your average cookie. These sugary little treats have a secret weapon that not only gives them their softer appearance but also adds to their rich flavor.

These Cinnamon Sugar Pillow Cookies have a cream cheese and powdered sugar center! You might not see much of it if you break the cookie apart and look inside, but you’re sure going to taste all the difference with just one bite.

Start by preheating your oven and preparing a cookie sheet with parchment paper. Then go ahead and whip up the filling by mixing cream cheese and powdered sugar. Set this aside and prepare the cookie dough.

Make little dough balls out of the dough, then split them in half and flatten out each half. Add a dollop of filling to one half, then place the other half on top and re-roll. Chill for 30 minutes, then roll each dough ball in a mixture of cinnamon and sugar. All that’s left to do is bake for 11 minutes and let cool. Go ahead and check out the recipe below!

Cinnamon Sugar Pillow Cookies

A different kind of cookie that's sure to be a hit!

Makes 16 cookies; 15 minutes to prepare, 11 minutes cook time, 30 minutes inactive

For the cookies:
  • 1 1/2 cup flour
  • 3/4 tsp baking soda
  • 1/2 tsp baking powder
  • 1/2 tsp salt
  • 1/2 cup sugar
  • 6 tbsp oil
  • 1 1/2 tbsp milk
  • 2 tsp pure vanilla extract
  • Equal parts cinnamon and sugar if desired for coating
For the filling:
  • 4 tsp powdered sugar
  • 1/4 cup cream cheese, room temp
Preparation
  1. Preheat oven to 325 F. Prepare a cookie sheet with parchment paper, set aside.
  2. For the filling, combine powdered sugar and cream cheese and mix until smooth. Set aside.
  3. For the filling, combine powdered sugar and cream cheese and mix until smooth. Set aside.
  4. In a mixing bowl, combine the dry ingredients (first five ingredients) and stir well.
  5. In a mixing bowl, combine the dry ingredients (first five ingredients) and stir well.
  6. Add in the oil, milk, and vanilla to form a cookie dough. (You can add extra milk if the dough seems too dry).
  7. Add in the oil, milk, and vanilla to form a cookie dough. (You can add extra milk if the dough seems too dry).
  8. Make little dough balls out of the dough, then split them in half and flatten out each half. Add a dollop of filling to one half, then place the other half on top and re-roll. Chill 30 minutes.
  9. 
Make little dough balls out of the dough, then split them in half and flatten out each half. Add a dollop of filling to one half, then place the other half on top and re-roll. Chill 30 minutes.
  10. 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.
  11. 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.

Recipe adapted from Chocolate Covered Katie