Preheat the oven to 350°F (175°C). Line baking trays with parchment paper to prevent sticking.
In a large mixing bowl, cream together the softened butter with both the granulated and brown sugars until the mixture becomes pale and fluffy. Add the eggs individually, beating well after each addition. Stir in the vanilla extract.
In a separate bowl, combine the flour, cocoa powder, baking soda, and salt. Whisk to blend evenly.
Gradually incorporate the dry ingredients into the butter mixture, mixing just until the dough comes together. Gently fold in the chocolate chips and cherries until evenly distributed throughout.
Using a spoon or small cookie scoop, portion the dough into rounded tablespoons and arrange them on the prepared baking sheets, ensuring at least 2 inches of spacing between each.
Bake in the preheated oven for 10 to 12 minutes, or until the edges have firmed up while the centers remain soft.
Allow the cookies to rest on the baking sheets for 5 minutes post-baking, then transfer them to a wire rack to cool completely.