In a medium bowl, beat the softened cream cheese, powdered sugar, and vanilla extract until completely smooth and creamy.

Line a small baking sheet or plate with parchment paper. Using a small cookie scoop or tablespoon, drop 14 equal mounds (approx 1 tablespoon each) onto the parchment. Freeze for at least 45 minutes until solid and easy to handle.

CRITICAL CHEF STEP: Spread the canned pumpkin puree onto a plate lined with 4 layers of paper towels, and press gently with 2 more paper towels to absorb excess moisture until reduced to about 1/3 cup. Blotting the pumpkin guarantees chewy, dense cookies instead of cakey mounds!

In a large bowl, whisk the melted butter, brown sugar, and granulated sugar for 1 minute until smooth. Whisk in the blotted pumpkin puree, egg yolk, and vanilla extract until glossy.

Add the flour, cream of tartar, baking soda, pumpkin pie spice, and salt. Switch to a spatula and fold gently just until no dry flour streaks remain. Chill dough in the refrigerator for 30 minutes for easy handling.

Preheat oven to 350°F (175°C). Line two large baking sheets with parchment paper. In a small shallow bowl, mix the granulated sugar and ground cinnamon.

Scoop 2 tablespoons of chilled dough, flatten into a disc in your palm, place a frozen cream cheese dollop in the center, and wrap the dough tightly around the filling, pinching the seams to seal completely. Roll into a smooth ball.

Roll each dough ball generously in the cinnamon sugar mixture until fully coated. Place 2 inches apart on the prepared baking sheets.

Bake at 350°F (175°C) for 11 to 13 minutes, until the edges are set and crackled with cinnamon sugar (the centers will still look very soft). Cool on the pan for 10 minutes before transferring to a wire rack. Serve warm for that molten cheesecake pull!