In a small bowl, mix cream cheese, powdered sugar, and 1 teaspoon vanilla extract until smooth. Scoop into 12 1/2-tablespoon mounds and freeze on a parchment-lined plate for at least 1 hour until solid. 4 ounces cream cheese,1/4 cup powdered sugar,1 teaspoon vanilla extract.
In a medium bowl, whisk together flour, baking soda, salt, and pumpkin pie spice. 2 cups all-purpose flour,1 teaspoon baking soda,1/2 teaspoon salt,1 teaspoon pumpkin pie spice.
In a large bowl, cream together softened butter, brown sugar, and white sugar until light and fluffy, about 2–3 minutes. Beat in the egg, pumpkin puree, and 1 teaspoon vanilla extract until fully combined. 1/2 cup unsalted butter,3/4 cup brown sugar,1/4 cup white sugar,1 large egg,1/2 cup pumpkin puree,1 teaspoon vanilla extract.
Stir the dry ingredients into the wet ingredients just until a dough forms. Cover and chill while the cream cheese filling continues to freeze.
Preheat oven to 350°F. Line baking sheets with parchment paper.
Using a large cookie scoop, scoop dough into balls and place on a parchment-lined plate or tray. Freeze for 10 minutes to firm up.
Remove from freezer and press each dough ball into a 3 1/2-inch wide disc using the back of a 1-cup measuring cup or a flat-bottomed object.
Place a frozen cream cheese ball in the center of each disc, then carefully fold the dough over the filling, pinching to seal completely. Roll into a smooth ball again and place on the prepared baking sheet about 2 inches apart.
Bake for 14–16 minutes, until edges are set and the cookies no longer look underbaked on top. Let cool on the pan for 5 minutes before transferring to a wire rack.
Notes
Pro Tip: Pumpkin makes for a naturally soft and moist cookie, so chilling the dough as directed is essential for holding its shape and achieving that perfect soft cookie texture. Freezing the cream cheese filling completely solid helps it stay neatly tucked inside while baking and gives you the best results.