Preheat the oven: 375°F (190°C). Line a baking sheet with parchment paper.
In a large bowl, mix all the wet ingredients: first, combine the oil and sugar until smooth. Then, add milk, egg, vanilla and pumpkin purée. Whisk again until creamy and glossy.
In a small bowl, whisk together all dry ingredients: fresh-milled flour (or substitute), pumpkin pie spice, salt, baking powder, and baking soda.
Stir the dry ingredients into the wet just until no streaks remain. Fold in chocolate chips. (The dough will be soft and a little bit sticky.)
Drop heaping spoonfuls onto the prepared baking sheet, leaving space between cookies. Bake for 10–12 minutes, or until the tops are set and no longer glossy. Mine takes 10 minutes.
Transfer cookies to a wire rack and let cool slightly before eating. Makes about 30 cookies.