Preheat your oven to 350°F (175°C) and position a rack in the middle. Grease a 9-inch round or square baking dish.
Prepare the cherry filling by combining pitted cherries, ¼ cup of granulated sugar, cornstarch, lemon juice, and almond extract in a bowl. Toss gently until cherries are evenly coated. Set aside for 10 minutes to allow juices to release.
Make the cobbler batter by whisking together flour, remaining ½ cup sugar, baking powder, and salt in a medium bowl. In a separate bowl, combine melted butter, milk, and vanilla extract. Pour the wet ingredients into the dry ingredients and stir just until combined.
Pour the batter into your prepared baking dish, spreading it evenly across the bottom. Do not stir after this point.
Spoon the cherry mixture evenly over the batter, including all the accumulated juices. The fruit will appear to sink, but the batter will rise around and through the cherries during baking.
Sprinkle the top with coarse sugar if using, for an extra crisp, sparkly crust.
Bake for 40-45 minutes until the topping is golden brown and a toothpick inserted into the cake portion comes out clean. The filling should be bubbling around the edges.
Allow the cobbler to cool for at least 15 minutes before serving to let the filling set slightly. Serve warm with vanilla ice cream or lightly whipped cream.