Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
Using an electric mixer, beat the softened butter, Swerve, egg yolk, and vanilla until smooth and creamy.
Drain excess liquid from pumpkin puree by squeezing it in paper towels over a bowl until about 1/4 cup remains. Mix the strained pumpkin into the butter mixture.
Add pumpkin pie spice, baking powder, xanthan gum, salt, and almond flour; stir until combined.
Gently fold in the chocolate chips with a spatula.
Form 24 one-inch balls, placing 12 on the baking sheet, then flatten each slightly.
Bake for 22-24 minutes until lightly browned, flipping sheets halfway.
Optional: sprinkle with kosher salt. Cool on the sheet for 10 minutes, then transfer to a wire rack.
Notes
Feel free to adjust sweetness by using more or less Swerve. These cookies are best enjoyed fresh but can be stored in an airtight container for a few days.