Make the cheesecake filling. In a small bowl, beat 8 oz softened cream cheese with 1/4 cup granulated sugar and 1/2 teaspoon vanilla until smooth.
Scoop 1-teaspoon mounds onto a parchment-lined plate. Freeze 20–30 minutes until firm. This makes stuffing the cookies easy.
Blot the pumpkin. Measure 1/2 cup pumpkin puree.
Spread it on a few layers of paper towels, top with another towel, and press gently to remove excess moisture. You want it thick, not watery. Scrape it back into a cup.
Cream the butter and sugars. In a large bowl, beat 1/2 cup unsalted butter with 1/2 cup brown sugar and 1/4 cup granulated sugar until light and fluffy, about 2 minutes.
Add wet ingredients. Beat in the blotted pumpkin, 1 large egg yolk, and 1 teaspoon vanilla.
Mix until combined. The mixture may look slightly curdled; that’s fine.
Whisk the dry ingredients. In a separate bowl, whisk 2 cups all-purpose flour, 1 tablespoon cornstarch, 1 teaspoon baking powder, 1/2 teaspoon baking soda, 1/2 teaspoon fine salt, 1 1/2 teaspoons ground cinnamon, 1/2 teaspoon ground ginger, 1/4 teaspoon nutmeg, and a pinch of cloves.
Combine. Add the dry ingredients to the wet and mix on low just until no dry streaks remain. The dough will be soft but should hold its shape.
Chill. Cover and chill the dough for 30–45 minutes.
This helps with rolling and keeps the cookies thick.
Preheat and prep. Heat the oven to 350°F (175°C). Line two baking sheets with parchment.
Assemble. Scoop about 2 tablespoons of dough (a medium cookie scoop). Flatten it in your palm, place a frozen cheesecake mound in the center, and wrap the dough around it, sealing the edges.
Roll gently into a ball and place on the sheet, spaced about 2 inches apart.
Optional sugar coat. For a hint of crunch and sparkle, roll the dough balls in a mix of 2 tablespoons granulated sugar and 1/2 teaspoon cinnamon.
Bake. Bake 11–13 minutes, until the edges look set and the tops are slightly puffed. They should still look soft in the middle. Don’t overbake.
Cool. Let cookies sit on the sheet for 10 minutes, then transfer to a rack.
The centers will finish setting as they cool.
Finish. Dust with powdered sugar if you like, or leave them plain. Enjoy slightly warm or at room temp.