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Line 2 baking sheets with parchment paper and preheat the oven to 350°F/180C.
Whisk the olive oil and sugar together in a large mixing bowl, creaming together until well combined. Then mix in the vanilla, molasses, egg, and egg yolk until well combined.
In a separate mixing bowl, whisk the all purpose flour, baking soda, baking powder, and salt together.
Add half of the flour mixture to the bowl of wet ingredients and gently fold with a rubber spatula until only a few streaks of flour are left. Pour in the rest of the dry ingredients and fold until no streaks of flour remain.
Scoop 6 cookie dough balls on each prepared baking tray, leaving 2-3 inches between. Bake for 11-14 minutes or until the edges are slightly golden brown. Let the trays cool before transferring the cookies to a wire cooling rack and enjoy!