Ingredients
Equipment
Method
Make and bake the cookies
- Heat the oven to 350°F with racks in the upper and lower thirds.
- Line two 18x13-inch baking sheets with parchment paper.
- Beat the softened unsalted butter and granulated sugar in a large bowl with an electric mixer on medium speed until light and fluffy, about 2 minutes.
- Beat in the egg yolk and vanilla extract until combined, scraping down the bowl as needed.
- Add the all-purpose flour and fine salt and mix on low just until no dry flour remains.
- Cover and refrigerate the dough for 30 minutes.
- Roll the dough into 24 balls, about 1 1/2 tablespoons each.
- Arrange 12 balls on each baking sheet, spacing them about 2 inches apart.
- Press a thumb or the rounded back of a 1/2-teaspoon measure into the center of each ball to make a well.
- Bake for 12–15 minutes, swapping the sheets between racks and rotating them front to back halfway through, until the edges are set and lightly golden.
- If the wells have puffed up, gently press them back down with the rounded back of the measuring spoon while the cookies are warm.
- Cool the cookies on the baking sheets for 5 minutes.
- Transfer the cookies to a wire rack to cool completely.
Fill the cookies
- Spoon 1 teaspoon pumpkin butter into the center of each cooled cookie.
Make and apply the maple icing
- Whisk the powdered sugar, pure maple syrup, and whole milk in a small bowl until smooth.
- Drizzle the icing over the cookies.
- Let the icing set for 15 minutes before serving.
Notes
For tidy centers, gently press down any puffed wells while the cookies are still warm, then fill only after they cool completely. Store in an airtight container in the refrigerator for up to 5 days; freeze for up to 2 months. For a dairy-free variation, use dairy-free butter and an unsweetened plant-based milk.