In a medium bowl, whisk together cocoa powder, granulated sugar, flour, baking powder, and salt. Set aside.
Using a stand mixer (or hand mixer + large bowl), add vegetable oil, eggs, and vanilla extract. Mix on low just long enough to break the egg yolks, about 10-15 seconds.
Keeping speed on low, pour in 1/3 of the dry ingredients to the mixing bowl, blending for 30 seconds to 1 minute. Continue adding the rest of the dry ingredients until cookie batter is thoroughly mixed. Batter will be dark and sticky.
Cover and chill cookie dough for at least 1 hour, ideally 4 hours, or up to overnight.
Preheat oven to 350 degrees F. Line a baking sheet with parchment paper. Place powdered sugar in a shallow bowl and keep it handy for the next step.
Scoop 1-2 tablespoons of cookie dough with a cookie scoop and roll it into a ball. Drop ball in powdered sugar and toss to coat completely. Place sugar coated cookie ball on the prepared baking sheet. Repeat this step until all the cookie dough batter is used, spacing cookies 2 inches apart.
Bake cookies for 10-13 minutes or until tops of cookies are lined with cracks (as pictured).
Let cookies cool on the baking sheet for 5 minutes before transferring to a wire cooling rack to cool completely.
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