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Prepare the Cinnamon Swirl Paste: In a small bowl, mix together the 2 tablespoons of dark brown sugar, 1 tablespoon of cinnamon, 1 tablespoon of melted unsalted butter, and 1 teaspoon of all-purpose flour until it forms a smooth paste. Set aside.

Prepare the Streusel Topping: In a medium bowl, mix together the 1/2 cup of all-purpose flour, 1/4 cup of brown sugar, 1 teaspoon of cinnamon, and a pinch of salt. Using a fork or your fingers, cut in the 4 tablespoons of cold unsalted butter pieces until the mixture is crumbly. Set aside (you can place it in the fridge if desired).
Prepare the Cookie Dough (Wet Ingredients): In a large bowl, cream together the 1 cup of soft unsalted butter, 3/4 cup of packed light brown sugar, and 1/4 cup of white sugar until smooth and light.

Add the egg, egg yolk, and 2 teaspoons of vanilla to the creamed butter and sugar mixture. Mix until well combined.

Prepare the Cookie Dough (Dry Ingredients): In a separate medium bowl, whisk together the 2 1/2 cups of all-purpose flour, 1/2 teaspoon of salt, 1 teaspoon of baking soda, and 1 teaspoon of cinnamon.

Combine Wet and Dry Ingredients: Gradually fold the dry ingredients into the wet ingredients, mixing until just combined. Be careful not to overmix.

Add Cinnamon Swirl: Dollop the prepared cinnamon swirl paste onto the cookie dough. Carefully fold it into the dough a few times to create a marbled look; do not overmix.

Chill the Dough: Scoop the dough onto a baking sheet (lined with parchment paper if desired) or into a bowl. Cover and set it in the fridge for at least 1 hour to chill. If the dough feels too wet to scoop initially, you can scoop it after it has chilled.

Preheat Oven and Prepare Baking Sheet: Once the dough is chilled, preheat your oven to 350°F (175°C). Line a baking tray with parchment paper.

Form and Top Cookies: Place the chilled dough balls onto the prepared baking tray, spacing them apart. Gently press down on each dough ball to slightly flatten it. Generously sprinkle the prepared streusel topping over each cookie dough ball.

Bake the Cookies: Bake for 11-13 minutes, or until the edges are golden brown and the centers are set. Baking time may vary depending on the size of your cookies.

Cool Cookies: Let the cookies cool fully on the baking sheet before transferring them to a wire rack.

Prepare the Vanilla Glaze: While the cookies cool, in a small bowl, mix together the 1/2 cup of powdered sugar, 1-2 tablespoons of water or milk, and 1/2 teaspoon of vanilla. Add more powdered sugar to thicken the glaze or more liquid to thin it, as desired, until you reach a drizzling consistency.

Glaze and Serve: Once the cookies are completely cool, drizzle the vanilla glaze generously over them. Serve and enjoy!


Prepare the Cinnamon Swirl Paste: In a small bowl, mix together the 2 tablespoons of dark brown sugar, 1 tablespoon of cinnamon, 1 tablespoon of melted unsalted butter, and 1 teaspoon of all-purpose flour until it forms a smooth paste. Set aside.

Prepare the Streusel Topping: In a medium bowl, mix together the 1/2 cup of all-purpose flour, 1/4 cup of brown sugar, 1 teaspoon of cinnamon, and a pinch of salt. Using a fork or your fingers, cut in the 4 tablespoons of cold unsalted butter pieces until the mixture is crumbly. Set aside (you can place it in the fridge if desired).
Prepare the Cookie Dough (Wet Ingredients): In a large bowl, cream together the 1 cup of soft unsalted butter, 3/4 cup of packed light brown sugar, and 1/4 cup of white sugar until smooth and light.

Add the egg, egg yolk, and 2 teaspoons of vanilla to the creamed butter and sugar mixture. Mix until well combined.

Prepare the Cookie Dough (Dry Ingredients): In a separate medium bowl, whisk together the 2 1/2 cups of all-purpose flour, 1/2 teaspoon of salt, 1 teaspoon of baking soda, and 1 teaspoon of cinnamon.

Combine Wet and Dry Ingredients: Gradually fold the dry ingredients into the wet ingredients, mixing until just combined. Be careful not to overmix.

Add Cinnamon Swirl: Dollop the prepared cinnamon swirl paste onto the cookie dough. Carefully fold it into the dough a few times to create a marbled look; do not overmix.

Chill the Dough: Scoop the dough onto a baking sheet (lined with parchment paper if desired) or into a bowl. Cover and set it in the fridge for at least 1 hour to chill. If the dough feels too wet to scoop initially, you can scoop it after it has chilled.

Preheat Oven and Prepare Baking Sheet: Once the dough is chilled, preheat your oven to 350°F (175°C). Line a baking tray with parchment paper.

Form and Top Cookies: Place the chilled dough balls onto the prepared baking tray, spacing them apart. Gently press down on each dough ball to slightly flatten it. Generously sprinkle the prepared streusel topping over each cookie dough ball.

Bake the Cookies: Bake for 11-13 minutes, or until the edges are golden brown and the centers are set. Baking time may vary depending on the size of your cookies.

Cool Cookies: Let the cookies cool fully on the baking sheet before transferring them to a wire rack.

Prepare the Vanilla Glaze: While the cookies cool, in a small bowl, mix together the 1/2 cup of powdered sugar, 1-2 tablespoons of water or milk, and 1/2 teaspoon of vanilla. Add more powdered sugar to thicken the glaze or more liquid to thin it, as desired, until you reach a drizzling consistency.

Glaze and Serve: Once the cookies are completely cool, drizzle the vanilla glaze generously over them. Serve and enjoy!
