These ultra soft cookies are stuffed with a melt-in-your-mouth cinnamon–brown sugar filling and finished with a buttery cinnamon-sugar glaze. They're packed with childhood nostalgia in every bite!
In a medium size bowl, whisk together the flour, cornstarch, baking soda, baking powder, and salt. Set this aside.
1 and ⅞ cup (225g) all-purpose flour, 1 Tablespoon (8g) cornstarch, ½ teaspoon baking soda, ¾ teaspoon baking powder, ½ teaspoon salt
In a large bowl with a handheld mixer or the bowl of a stand mixer fitted with the paddle attachment, cream the butter and both sugars on medium-high speed until the mixture is light in color and fluffy in texture, about 2-3 minutes. Add the egg and vanilla extract and beat again until everything is incorporated.
½ cup (113g) unsalted butter, ½ cup (100g) firmly packed light brown sugar, ¼ cup (50g) granulated sugar, 1 large egg, ½ teaspoon vanilla extract
With the mixer in low, gradually add the dry ingredients to the wet ingredients and beat until completely combined, stopping to scrape down the sides and bottom of the bowl as necessary. Cover the dough and chill it in the refrigerator for at least 1 hour and up to 3 days.
FILLING
When you are ready to bake the cookies, preheat the oven to 350ºF (177ºC). Line two large baking sheets with parchment paper or a silicone baking mat. Set aside.
Add the brown sugar, softened butter, flour, and cinnamon to a small bowl. Use a spatula or a spoon to smash and blend the ingredients together until you have a cohesive mixture. Set aside.
⅜ cup (75g) firmly packed light brown sugar, 2 Tablespoons (28g) unsalted butter, 1 Tablespoon (8g) all-purpose flour, ½ teaspoon ground cinnamon
Use a cookie scoop that is about 1 Tablespoon in size (I use this #50 cookie scoop for all of my standard size cookies) to drop balls of dough onto one of the baking sheets (don't worry about spacing them out just yet). Count how many cookie dough balls you have and divide this number by two-- this is how many balls of filling you will need to make (each cookie uses two dough balls with a ball of filling sandwiched inside). If you have an odd amount of cookie dough balls, that's ok! You can make one smaller cookie by dividing that ball of dough in half.
Divide the filling into as many portions as you need. You can place them on the baking sheet with the cookie dough balls or a separate plate/surface. I like to use a mini cookie scoop (1 teaspoon size) to make heaping teaspoons of filling. Each of my filling balls was about 1 and ½ to 2 teaspoons in size. Once you have portioned out the filling, roll each one into a smooth ball.
Working with one pair of cookie dough balls at a time, use your hands to gently flatten each cookie dough ball slightly. Place a ball of filling into the middle of one of the dough balls, then place the other slightly flattened cookie dough ball on top to create a sandwich. Use your fingers to press the seams together, then gently roll the cookie dough ball with your hands to smooth out the surface. Place filled cookie dough ball onto the second prepared baking sheet, placing no more than 6 of them on a baking sheet at a time.
Bake the cookies for for 10-12 minutes, until the tops are just set and the edges are just starting to turn golden brown. Allow cookies to cool on the baking sheet for at least 5 minutes before transferring to a cooling rack to cool completely.
GLAZE
In a small bowl, whisk together the powdered sugar, butter, milk, and cinnamon until smooth. Place the cooling rack over a baking sheet or piece of parchment paper.
½ cup (60g) powdered sugar, 1 Tablespoon (14g) unsalted butter, 1 Tablespoon (15mL) milk, ¼ teaspoon ground cinnamon
Use a spoon to portion about 1 scant teaspoon of icing on top of each cookie and use the back of the spoon to spread it to the edges of the cookie (it's ok if some of it runs off the edge). Allow the icing to set before enjoying, about 30 minutes. Store cookies covered tightly at room temperature for up to 5 days. Cookies freeze well, up to 3 months, with or without icing. Thaw at room temperature. Cookie dough balls freeze well, up to 3 months. Thaw in the refrigerator before baking.
All nutritional values are approximate and provided to the reader as a courtesy. Changing ingredients and/or quantities will alter the estimated nutritional calculations.