Preheat oven to 350°F. Line two large cookie sheets with parchment paper or silicone baking mats.
In a large bowl whisk together the sweet potato, milk, molasses, and vanilla). In a medium bowl stir together the oat flour, baking powder, baking soda, and salt). Add flour mixture to sweet potato mixture; stir until combined. Stir in chocolate chips.
Using a cookie scoop or 1½-tablespoons portions, drop dough 2 inches apart on prepared cookie sheets. Flatten cookies to 2-inch diameter. Bake 8 to 10 minutes or until lightly browned. Let cool 2 minutes on cookie sheets. Remove and cool on wire racks.