Preheat your oven to 350°F (convection) and line a baking sheet with parchment paper.

In a medium bowl, mix the room-temperature cream cheese, well-drained pumpkin purée (use a cheesecloth or clean kitchen towel to remove excess moisture), powdered sugar, vanilla, and pumpkin pie spice until smooth.

Scoop 1-tablespoon portions onto a parchment-lined plate or tray and freeze until firm while you prepare the dough.

In a stand mixer fitted with a whisk or paddle attachment, beat the room-temperature butter and granulated sugar for 1–2 minutes, until light and off-white.

Mix in the egg and vanilla extract until fully combined.

Add the all-purpose flour, baking powder, and baking soda. Mix on low speed or fold gently just until the dough comes together.

In a small bowl, mix together the brown sugar swirl ingredients: brown sugar, cinnamon, pumpkin purée, all-purpose flour, and pumpkin pie spice. The mixture should be slightly chilled before using.

Scoop ⅓ cup portions of cookie dough and gently fold in about 2 teaspoons of the brown sugar mixture. Flatten the dough in your palm, place a chilled pumpkin cheesecake ball in the center, then wrap the dough around it to seal. Roll each dough ball in granulated sugar.

Repeat with remaining dough.

Place the filled cookie dough balls onto the prepared baking sheet, spacing evenly.

Bake for 12–13 minutes, until the edges are set and the centers are soft.

Immediately after baking, use a round bowl, cup, or cookie cutter to gently swirl around each cookie for clean, circular edges.

Let cookies cool on the baking sheet for about 10 minutes before removing.

Enjoy fresh, or store in a chilled environment for up to 8 days.