Line 2 baking sheets with parchment paper. Line a small cutting board or tray that will fit in your freezer with parchment paper or plastic wrap.
In a large mixing bowl, beat the butter and brown sugar on high speed until well combined and light.
1/2 cup unsalted butter, softened, 1 cup light brown sugar
Beat in the egg yolk, vanilla and pumpkin puree just until combined.
1 large egg yolk, 1 1/2 teaspoons vanilla extract, 1/4 cup canned pumpkin puree
Sprinkle the pumpkin pie spice, cinnamon, baking powder and salt over the mixture and beat for a few seconds, just until combined.
1/2 teaspoon pumpkin pie spice, 1/2 teaspoon ground cinnamon, 1 teaspoon baking powder, 1/4 teaspoon salt
Add the flour. Use a silicone spatula to partially incorporate it, then mix on low speed just until combined.
1 1/2 cups flour
Divide the dough into eighteen 33-gram balls. Place them on the prepared board or tray and freeze for 1 hour. If you freeze them longer, let them sit at room temperature just until they are soft enough to flatten.
Meanwhile, prepare the cheesecake filling. Beat the cream cheese and granulated sugar on medium speed until light and fluffy. Mix in the vanilla and salt.
6 ounces cream cheese, 3 tablespoons granulated sugar, 1/2 teaspoon vanilla extract, Pinch of salt
Line another small board or tray with parchment paper or plastic wrap. Portion the filling into eighteen 11-gram (about 2-teaspoon) mounds. A small cookie scoop works well for this. Don’t flatten the filling into discs because you’ll be wrapping the dough around the frozen portions. Freeze for 1 hour, or until firm.
Toward the end of the freezing time, preheat the oven to 350 °F (175 °C). Stir together the coarse/raw sugar and cinnamon in a small bowl.
2 tablespoons coarse/raw sugar, 1 teaspoon ground cinnamon
Flatten one firm cookie dough ball in the palm of your hand and place a frozen cheesecake filling portion in the center. Bring the edges of the dough up and around the filling to form a ball, making sure the cheesecake is covered. You can also flatten the dough between two pieces of parchment paper. Repeat with the remaining dough and filling.
Roll each filled cookie dough ball in the cinnamon sugar and place about 3 inches apart on the prepared baking sheets. Do not flatten them.
Bake for 14-16 minutes, or until the cookies have cracked and feel firm on top.
Let cool for 5 minutes on the baking sheet, then transfer to a wire rack to cool completely. Refrigerate leftovers in an airtight container for up to 5 days.