Holiday Cookie Countdown: Cinnabon Pinwheels


These amazing cookies almost didn’t make the cut because I messed them up the first time I made them. I wasn’t paying attention to how I was supposed to roll them out (the directions say a 12-13-inch square). I rolled the dough waaaaaaay too thin, like a pie crust, and it was a mess to roll up. The cookies were not pretty. I actually took a picture and was going to put in a bloopers post for later.

But then I tasted one.

Oh Em Gee. It was so good.

Something about the hint of orange married with the vanilla and cinnamon in the most tender cookie imaginable (despite the fact that I massacred it) — I knew I had to make it right.

So I made them again and then had a friend make them. Both times, when we followed the directions, they turned out perfect. Lesson learned. Follow the darn directions.

Got it?

Holiday Cookie Countdown: Cinnabon Pinwheels

Holiday Cookie Countdown: Cinnabon Pinwheels


for the cinnamon butter filling:

5 tablespoons plus 2 teaspoons unsalted butter, softened

1/4 cup packed light brown sugar

1-1/2 teaspoons light corn syrup

1 tablespoon ground cinnamon

2 tablespoons all-purpose flour

1/2 teaspoon salt

1/2 teaspoon pure vanilla extract

for the dough:

1 cup unsalted butter at room temperature

1/3 cup granulated sugar

3/4 cup confectioners' sugar

1/2 teaspoon salt

1-1/2 teaspoons grated orange zest

1 teaspoon pure vanilla extract

1 large egg

2-1/4 cups all-purpose flour

for the glaze:

1/2 cup confectioners' sugar

2 tablespoons light corn syrup

1 teaspoon pure vanilla extract

1 teaspoon water


Use a mixer to combine all of the cinnamon butter filling ingredients and beat on medium speed until light and fluffy, about 2 or 3 minutes. Set aside.

In the bowl of a stand mixer fitted with the paddle attachment, beat the butter, sugars, salt, zest, and vanilla together on medium speed until light and fluffy, about 3 or 4 minutes. Scrape down the sides of the bowl and add the egg, beating well to incorporate.

Turn the mixer down to low and add the flour, mixing until just barely combined.

On a sheet of wax or parchment paper (whatever your preference), roll the dough out to approximately 12 to 13-inch square. When it comes time to roll into a log, the paper makes it easier to lift the edge and handle the dough.

Spread the cinnamon butter filling on top of the rolled out cookie dough.

Roll the dough into a log shape. Once you get an edge started rolling by just folding it over slightly, you can simply lift the paper edge and use it to guide the dough to continue rolling. Don't worry if the ends are uneven; you can just smoosh them in to form a flat edge. The first slice from each end will not have the pretty spiral, but there won't be any wasted dough.

Wrap the log in plastic wrap or the parchment paper you used to roll it out and gently squeeze the log to ensure there are no air pockets inside. You can then roll the log a few times to smooth it back out if necessary.

Transfer the dough to the freezer for at least 15-20 minutes, until firm.

When ready to bake, preheat the oven to 375°F.

Remove the dough log from the freezer and using a sharp knife, cut the dough into 1/4" slices. Give the log a quarter roll after each cut so it doesn't develop a flat edge from constantly pressing on the same side.

Transfer the cut slices to your prepared cookie sheets and bake for about 12-14 minutes, rotating the baking sheet halfway through, until they’re lightly golden around the edges. Allow to cool on a wire rack for a few minutes before removing the cookies from the pan and allowing them to cool completely.

Combine all the ingredients for the glaze in a small bowl and whisk together. Add additional water if it seems too thick. Using a pastry brush, apply a thin coat to the top of each cookie. Allow to sit at room temperature to dry completely.

Makes 40-45 cookies.

Adapted from Wanna Come With who adapted from The Culinary Institute of Americe/Todd Knaster

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