Cinnamon Orange Pinwheel Cookies

Close-up of a cinnamon orange pinwheel cookie with drizzles of icing zigged zagged across the top of the cookie.

5 from 2 votes

Cinnamon Orange Pinwheel Cookies

Cinnamon rolls are so decadaent, but making them into cookie form gives you all the flavor without being quite so heavy.

Prep Time20

Total Bake Time33

Chill3

Total Time3 53

Course: Cookies

Cuisine: American

Difficulty: Medium

Servings: cookies

Calories: 167kcal

Ingredients

COOKIE DOUGH

1 cup (227 g) Butter unsalted room temperature
4 oz (4 oz) Cream Cheese room temperature
1 ½ cup (300 g) Sugar white
2 (2) Eggs room temperature
1 teaspoon (1 teaspoon) Vanilla bean paste
3 cups (375 g) All-purpose flour
½ teaspoon (0.5 teaspoon) Kosher Salt
1 ¼ teaspoon (1.25 teaspoon) Baking powder
1 tablespoon (1 tablespoon) Orange juice fresh
1 tablespoon (1 tablespoon) Orange zest

FILLING

3 tablespoon (3 tablespoon) Butter unsalted melted
1 ½ tablespoon (1.5 tablespoon) Ground cinnamon
¼ cup (50 g) Sugar white
¼ cup (55 g) Light brown sugar

ICING

1 cup (120 g) Powdered sugar
½ teaspoon (0.5 teaspoon) Vanilla Extract
2-4 tablespoon (2 tablespoon) Milk
1 tablespoon (1 tablespoon) Butter unsalted melted

Instructions

COOKIE DOUGH

Weigh or measure the sugar and set it aside. Weight or measure the flour, salt, and baking powder in another bowl and run a whisk through to blend. Zest and juice one orange into separate containers and set these aside also.
In a stand or hand-held mixer, cream the butter and cream cheese until mixed, about 1 to 2 minutes. Then add the sugar and mix for another 2 to 3 minutes. You want it light and fluffy looking. Add one egg at a time, mixing the first thoroughly before adding the second egg. Next, mix the vanilla bean paste, orange zest, and orange juice for about a minute. Scrape down the sides of the bowl and turn your mixer to low. Slowly add the flour mixture until incorporated.
Depending on how tacky the cookie dough this will guide you on how much flour to spread out before adding the cookie dough to the pastry mat. Add what you need to work with the dough. Divide the cookie dough in half and flatten the halves into flattened rectangles. The rectangular shape will make it easier to roll out. Wrap both halves in separate plastic wrap. I put them on a sheet pan and into the refrigerator for at least 2 hours.

FILLING AND PUTTING THE PINWHEEL TOGETHER

Rolling out the rectangular cookie dough shape works well on parchment paper. First, roll the cookie dough about ½-inch thick, covering most of the parchment paper. Then, take your hands and shape any dough that is sticking out of the rectangle shape.
In a small bowl, add the melted butter, cinnamon, white sugar, and light brown sugar, mixing it to combine. If it is a little stiff, microwave it for about 10 seconds. Then, using half of the filling, spread small spoonsful around the cookie dough rectangle. Now, smear the filling using your hands, leaving a good inch or two around the edges. Time to roll!
To roll, pick up the short end of the parchment paper and start to roll the cookie dough. Gravity helps to make the log. Just before completing the log, cut off a piece of plastic wrap about 4 inches longer on each side than the log, and lay it at the end of the log. Then lift the parchment paper to roll it right onto the plastic wrap. I pat the ends to square off the sides and then wrap them with plastic wrap.
I saw a neat trick where you split a paper towel roll in half and use the half to cradle the log. I was using this method for quite a while until I saw a baguette pan which is what I use now. Refrigerate for 1 to 2 hours. The colder the logs are, the easier they are to slice.
Preheat your oven to 350°F (175°C or 180°C), and line 2 cookie sheet pans with parchment paper and set aside. Take one log roll out of the refrigerator, slice about ½ thick slices, adding 12 to a pan. Give the cookie slices 2 inches between each other; they spread a little—Bake for 10-12 minutes. You want them to be a light golden brown on the bottom. After removing them from the oven, let them sit for a minute before moving them to a cooling rack.

ICING

Add the powdered sugar, vanilla extract, melted butter, and 2 tablespoon of milk in a small bowl and stir with a whisk. If the icing is too thick, add one more tablespoon of milk at a time until you get the right consistency. You want it thin enough to put some on a spoon and go back and forth across the top of each cookie.

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