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Cranberry Pillow Cookies Stuffed with Maple Cream Cheese

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Cranberry Pillow Cookies

My pillow may very well be my favorite place in the world – soft and inviting, it’s a place to rest my head and drift away from the day.

Like my pillow, these cranberry pillow cookies are soft and inviting and are stuffed with something fluffy (maple cream cheese) – but please don’t sleep on them.

These cranberry pillow cookies were universally loved by everyone I served them to, even those who typically prefer crunchy cookies.  I think it’s the surprise inside that won them over, but it could also be the winning combination of seasonal flavors.

How Do You Get the Filling Into Pillow Cookies?

Stuffing pillow cookies couldn’t be any easier.  Take one circle of cookie dough, put filling on top of it, top with another circle of cookie dough, and use your fingers to seal the edges of the two cookies together.  If you don’t like the idea of maple cream cheese, you can stuff pillow cookies with just about anything: more cranberry sauce or jam, nuts, dried fruit, or even pieces of cake or brownies.


Cranberry Pillow Cookie Recipe

The Complete Cookie

These cranberry pillow cookies are adapted from a recipe for apple honey pillows found in this book.  The recipe called for apple butter in the dough and an apple butter filling.  I didn’t have any apple butter in the house, but I did have cranberry sauce, so I decided to try the same technique with a little twist.  Someday, maybe for Rosh Hashana (the Jewish holiday where it’s customary to eat apples and honey), I’ll try the recipe as written.

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R.W. Knudsen Cranberry Sauce, 10 oz

Since cranberry sauce can mean different things to different people, I wanted to clarify that this was the brand of cranberry sauce I used.  It’s thick like a jam and it’s just a mixture of cranberries, fruit syrup, and water.

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Cranberry Pillow Cookies
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Cranberry Pillow Cookies Stuffed with Maple Cream Cheese

Servings 1 dozen fairly large pillow cookies


Cookie Ingredients

  • 1 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon salt
  • 1/2 cup unsalted butter room temperature
  • 1/2 cup light brown sugar
  • 1/2 cup cranberry sauce

Maple Cream Cheese Filling Ingredients

  • 4 ounces cream cheese room temperature
  • 2 tablespoons pure maple syrup


Cookie Instructions

  1. In a small mixing bowl, whisk together flour, baking powder, baking soda, and salt.
  2. In a medium-sized mixing bowl, beat the butter for several minutes until light and fluffy.
  3. Mix in the brown sugar and the cranberry sauce.
  4. Mix in the flour mixture a little bit at a time until just combined.
  5. Form into a log that's about 6 inches long and 1 1/2 inches tall.
  6. Wrap in parchment paper and refrigerate overnight.

Assembly and Baking Instructions

  1. When you are ready to bake, prepare the filling by thoroughly mixing the cream cheese and maple syrup.
  2. Preheat oven to 350 F.
  3. Using a sharp knife, slice chilled cookie dough into 1/4 inch discs.
  4. Place half the slices on parchment-lined cookie sheets at least 2 inches apart (they grow a lot in the oven). If the dough splits at all during this process, just push it back together. It's no big deal.
  5. Place 1 to 1 1/2 teaspoons of filling in the center of each disc on the cookie sheets.
  6. Top with remaining discs and press around the edge of each disc to join the halves together. Don't worry if the top cookie cracks a little bit; it will look fine after it bakes.
  7. Bake for 15 minutes or until lightly browned.
  8. Cool on wire racks.
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