Preheat oven to 400°F. Line a baking sheet with parchment paper. Spread halved cherries on the sheet, sprinkle with sugar, and bake for 10 minutes. Set aside.

Reduce oven temperature to 350°F. Spray a 9x9-inch baking dish with nonstick spray.

Combine ½ cup chocolate chips and oil in a microwave-safe bowl. Microwave in 15-second intervals, stirring until melted.

In a stand mixer, beat sugar, brown sugar, eggs, and vanilla on high for 5-6 minutes until light and doubled in size.

Turn mixer to low and slowly pour in melted chocolate mixture, mixing until just combined.

In a small bowl, whisk together flour, cocoa powder, and salt.

Add dry ingredients to wet ingredients, mix until just combined. Fold in remaining chocolate chips and roasted cherries.

Pour batter into prepared baking dish.

Bake for 30-35 minutes until a toothpick inserted comes out with crumbs but no wet batter.

Top with remaining roasted cherries. Cool before slicing and serving.