Ingredients
Scale
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg, room temperature
- 2 teaspoons alcohol-free vanilla extract
- 3 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/2 teaspoon salt
- 1 cup light brown sugar, packed (for filling)
- 1 tablespoon ground cinnamon (for filling)
- 1 tablespoon all-purpose flour (for filling)
- 4 tablespoons unsalted butter, melted (for filling)
- 1 1/2 cups powdered sugar (for glaze)
- 1/2 teaspoon ground cinnamon (for glaze)
- 1/2 teaspoon alcohol-free vanilla extract (for glaze)
- 2-3 tablespoons milk
Instructions
- Preheat your oven to 350°F (175°C) and line two large baking sheets with parchment paper
- In a large mixing bowl or stand mixer, cream the softened butter and granulated sugar together for 2-3 minutes until light and fluffy, then beat in the egg and alcohol-free vanilla extract until combined
- In a separate bowl, whisk together 3 cups flour, baking powder, and salt, then gradually add this to the wet ingredients, mixing on low speed just until a soft dough forms
- Prepare the filling by mixing the brown sugar, 1 tablespoon cinnamon, 1 tablespoon flour, and melted butter in a small bowl until it resembles wet sand
- Scoop about 3 tablespoons of dough and flatten it into a disc in your palm; place a scant tablespoon of the brown sugar filling in the center
- Gently fold the edges of the dough up and over the filling, pinching to seal it completely inside, then roll into a smooth ball and place on the baking sheet
- Repeat with remaining dough, spacing cookies 3 inches apart, and gently press down on each ball with the bottom of a glass to slightly flatten into a thick puck
- Bake for 10-12 minutes until the edges are just barely set and the centers still look soft; do not overbake or they will lose their fudgy texture
- Allow cookies to cool on the baking sheet for 10 minutes before transferring to a wire rack to cool completely
- Whisk together powdered sugar, 1/2 teaspoon cinnamon, alcohol-free vanilla, and milk until smooth, then spoon the glaze over the cooled cookies and let set before serving
Notes
For the best texture, make sure the butter for the dough is softened but not melted. If the glaze is too thick, add more milk a teaspoon at a time; if too thin, add more powdered sugar. Store in an airtight container at room temperature for up to 4 days.
- Prep Time: 25 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 385
- Sugar: 32g
- Sodium: 140mg
- Fat: 16g
- Saturated Fat: 10g
- Unsaturated Fat: 5g
- Trans Fat: 0.5g
- Carbohydrates: 58g
- Fiber: 1g
- Protein: 4g
- Cholesterol: 45mg