Preheat your oven to 400°F (200°C). Prepare the cherries by washing, halving, and pitting them. Toss with granulated sugar and roast for about 10 minutes.
Lower the oven temperature to 350°F (175°C) and prepare a 9x9-inch baking dish with non-stick spray.
In a microwave-safe bowl, combine ½ cup of chocolate chips with vegetable oil. Heat in 15-second intervals until melted.
In a stand mixer, mix granulated sugar, light brown sugar, eggs, and vanilla extract until light and creamy.
Slowly mix in the melted chocolate until well combined.
In a separate bowl, whisk together flour, cocoa powder, and salt.
Fold the dry mixture into the chocolate batter, then fold in the remaining chocolate chips and half of the roasted cherries.
Pour the batter into the prepared dish and bake for 30-35 minutes until a toothpick comes out with moist crumbs.
Let cool, top with remaining roasted cherries, and cut into squares.