Preheat the oven to 350°F (175°C). Cover a baking sheet with parchment paper and reserve it for the portioned cookie dough.

Place the room-temperature butter and granulated sugar in the bowl of a stand mixer fitted with the paddle attachment. Beat at medium speed for approximately 2 minutes, or until the mixture becomes pale, airy, and fluffy.

Add the molasses, pumpkin purée, vanilla extract, baking soda, kosher salt, and pumpkin pie spice. Continue mixing at medium speed for 1 minute, pausing to scrape down the sides of the bowl as necessary, until the mixture is evenly blended and smooth.

Lower the mixer speed and gradually incorporate the all-purpose flour. Mix only until the final visible streaks of flour disappear. Avoid prolonged mixing to preserve the cookies’ soft, delicate texture.

Measure the dough with a medium cookie scoop that holds approximately 2 tablespoons. Shape each portion into a ball and arrange the dough balls on the lined baking sheet, allowing roughly 2 inches of space between them.

Bake for about 9 minutes, or until the surfaces appear just set. Remove the cookies from the oven and transfer them to a wire cooling rack. Allow them to cool completely before applying the icing.

Whisk the sifted confectioners’ sugar, vanilla extract, and milk together until a smooth, uniform glaze forms.

Dip the top of each cooled cookie into the prepared icing. Place the glazed cookies aside until the coating has fully set.