In a medium mixing bowl, whisk together the gluten free flour, cocoa powder, baking powder, and salt until combined. Set aside.
In a large mixing bowl, beat the oil and granulated sugar on medium-high speed until the mixture is light and fluffy, about 2 minutes.
Reduce the speed to low and add 1 egg at a time until combined.
Add in the vanilla extract and beat on low speed until combined.
Add the flour mixture in 2 or 3 portions, and beat on low speed after each addition until completely combined.
Transfer the dough to a smaller bowl. Cover the bowl with plastic wrap and chill in the refrigerator for at least 2 hours.
When you're ready to bake the cookies, preheat the oven to 350 degrees. Line baking sheets with parchment paper.
Place the powdered sugar in a small bowl. Roll the dough into 1-inch balls, then roll dough balls in powdered sugar and coat completely. Place on the prepared baking sheets at least 2 inches apart.
Bake for 10 minutes. Allow the cookies to rest on the hot cookie sheets for 2 minutes, then transfer to a wire rack to cool completely.
Chilling the dough for a minimum of 2 hours is a necessary step. The chilled dough is easier to work with and will add a chewy texture to the cookies. You can make the cookies in two stages. Prepare the dough, refrigerate overnight, then roll and bake the cookies the next day.
Use a teaspoon to scoop enough dough out of the ball to create a 1-inch ball. Spray your hands with non-stick cooking spray or wet your hands with water to keep the dough from sticking while you roll it into balls. When the dough starts to stick, wash your hands and repeat.
Roll all the dough into balls and place on the prepared baking sheets. After all the dough balls are made, roll them in powdered sugar and place back on the baking sheets.
Completely coat the dough balls in powdered sugar. The powdered sugar gives the cookies their signature crinkle.
Don’t over bake the cookies. Over baking will lead to hard and crunchy cookies.
Allow the baked cookies to cool for 2 minutes on the baking sheet. The freshly baked cookies are delicate and need a couple of minutes to set up before being transferred to a wire rack to finish cooling.