Preheat oven to 350 degrees Fahrenheit. Line baking sheets with a silicone baking mat or parchment paper.

In a medium bowl, whisk together the flour, pumpkin pie spice, baking powder, baking soda, and salt. Set aside.

In a large bowl, whisk together the oil, brown sugar, granulated sugar, egg, pumpkin, and vanilla. Fold in dry ingredients until just combined. Dough will be thick, soft, wet and sticky.

Place sugars for rolling in two separate bowls. Use a #50 scoop (a heaping Tablespoon) and drop batter directly into the bowl of granulated sugar. Swirl bowl or use a spoon to coat the dough in sugar. Shake off excess. Roll dough in hands to smooth edges. Then coat the dough in powdered sugar. Do NOT shake off excess. Squeeze the powdered sugar gently around the dough and place it on the prepared baking sheet 2-inches apart. (Dough may spread/flatten some before baking. It is quite soft. This is ok.) Repeat process quickly to fit 12 cookies on the pan. Bake immediately. (Prepare cookies just before placing in oven. If the dough sits too long it will absorb the powdered sugar.)

Bake at 350˚F for 9-10 minutes, until puffy and cracked. The cookies should be soft and matte (not wet/shiny) where the cracks are. Do not over-bake. Cool slightly, then transfer to a wire rack to cool completely. Store in an airtight container at room temperature.