Preheat the oven to 350 degrees Fahrenheit. Line a baking sheet with parchment paper. Set aside.
In a medium bowl, mix together the gluten free flour, cocoa powder, baking powder and salt.
In a small bowl, using a spoon, mix together the cornstarch and water until thin and watery. It will be thick and tacky at first. Set aside.
In a large bowl, whisk together the vegetable oil, the dark brown sugar and vanilla until soft and creamy. Switch to using a spatula to combine when it starts getting thicker.
Slowly whisk the cornstarch water into the sugar mixture until fully combined. It will appear liquidy. That’s normal.
Starting and ending with the gluten free flour mixture, mix in some flour then some milk then some flour. Use a spatula to combine.
Once combined, use clean hands to knead everything into a dough. This should only take a few times before it all comes together. You can of course use a hand held mixer or electric mixer if you prefer.
Gently fold in ½ cup plus 2 tablespoons of chocolate chips using a spatula. This may be a bit tricky due to the shiny dough. I like to help mix them in with clean hands.
Separate the dough into 6 equal pieces and roll the dough into 6 balls. They will appear quite oily due to the olive oil. Don't worry, they won't be oily once baked.
Place the cookies on the baking sheet about 4 inches apart. Gently press down on the tops of the dough balls so they form a thick disc.
The dough is very sticky and may stick to your hands if they're warm. If this happens, rinse your hands and then shake off any excess water. You want them slightly wet but not dripping wet. This will help prevent the dough from sticking.
Whatever chocolate chips might have fallen out during rolling them into balls, press those extra chips into the tops of the cookies. If no chips fell out, feel free to add additional chips into the tops of the cookies.
Bake the cookies in the center rack of the oven at 350 degrees Fahrenheit for 13 minutes.
Immediately reshape the cookies when they come out of the oven by using a spatula to push them into a circle shape and let cool on the baking sheet for 2 min before transferring to a cooling rack. If you don't do this, the cookies will break apart into a giant mess.
