Make the cheesecake centers: Beat cream cheese, powdered sugar, vanilla, and a pinch of salt until smooth. Scoop into 16 small mounds (about 2 teaspoons each) onto a parchment-lined plate.
Freeze 30–45 minutes until firm.
Whisk the dry ingredients: In a bowl, combine flour, cornstarch, baking soda, baking powder, salt, cinnamon, ginger, nutmeg, and cloves if using.
Mix the wet ingredients: In a large bowl, whisk melted cooled butter, brown sugar, and granulated sugar until glossy. Whisk in egg yolk, pumpkin puree, and vanilla until smooth. For best texture, blot the pumpkin with paper towels to remove excess moisture before adding.
Bring the dough together: Add dry ingredients to wet and stir with a spatula just until no dry spots remain.
The dough will be soft but not sticky.
Chill briefly: Cover and refrigerate the dough for 30 minutes. This makes shaping easier and prevents spreading.
Prep to bake: Heat oven to 350°F (175°C). Line two baking sheets with parchment.
Mix 2 tablespoons sugar and 1 teaspoon cinnamon in a small bowl for rolling.
Shape the cookies: Scoop 16 portions of dough (about 2 tablespoons each). Flatten a portion in your palm, place a frozen cheesecake mound in the center, and wrap the dough around it. Pinch to seal completely.
Coat and arrange: Roll each ball in the cinnamon sugar.
Place on baking sheets spaced a few inches apart. Gently flatten the tops just a touch with your palm.
Bake: Bake 11–13 minutes, until the edges look set and the tops are slightly puffy but still soft. Do not overbake—carryover heat will finish them.
Cool: Let cookies rest on the sheet for 10 minutes, then transfer to a rack.
The centers will stay creamy but set as they cool.