Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper and set them aside while you prepare the cookie dough. This ensures the cookie dough won’t stick and makes for easy cleanup.

In the bowl of an electric mixer fitted with the paddle attachment, cream together the unsalted butter, light brown sugar, and granulated sugar. Beat on medium speed until the mixture is light and fluffy, which should take about 2 to 3 minutes. This step helps to aerate the butter and ensures the cookies will be tender.

Add the pumpkin puree, egg, and vanilla extract to the butter-sugar mixture. Mix until smooth and fully incorporated. With the mixer on low speed, gradually add the all-purpose flour, baking soda, baking powder, salt, and pumpkin pie spice. Mix just until combined—avoid overmixing the dough to keep the cookies tender. I like to scrape down the sides of the bowl to make sure everything is evenly mixed.

Using a cookie scoop about 1.5 inches in diameter, drop mounds of cookie dough onto the prepared baking sheets, spacing them 2 to 3 inches apart to allow for spreading. Bake the cookies in the preheated oven for about 12 minutes or until the edges are golden brown. Once baked, transfer to a wire rack and allow to cool for about 30 minutes before adding the glaze.

While the cookies are cooling, make the glaze. In a medium saucepan over medium heat, melt the butter and dark brown sugar together. Cook, stirring constantly, until the mixture is bubbly and thick, about 1 minute. Remove from heat and stir in the milk. Blend in the sifted powdered sugar until the glaze is smooth. For extra flavor, I sometimes add a tiny pinch of salt or a dash of vanilla to the glaze at the end.

Once the cookies have cooled, spoon the warm glaze over the tops of each cookie, letting it drip down the sides. Allow the glaze to set before serving. Enjoy these soft pumpkin cookies as a sweet treat for any fall gathering!