Preheat your oven: Start by preheating your oven to 350°F (175°C). Grease a 9x13-inch baking dish to prepare for the cherry filling.
Prepare the cherries: In a large mixing bowl, combine 4 cups cherries, 1/2 cup sugar, 1 tbsp cornstarch, 1 tsp vanilla, and 1 tsp almond extract (if using). Stir gently until the cherries are well-coated in the mixture. Spread this filling evenly in the prepared baking dish.
Combine dry ingredients: In a separate mixing bowl, whisk together 1 cup flour, 1 tsp baking powder, 1/2 cup sugar (reserve the rest for the cherry mixture), and 1/4 tsp salt.
Mix wet ingredients: In another bowl, whisk together 1/2 cup milk, 1/4 cup melted butter, and 1 large egg until well blended.
Combine wet and dry ingredients: Pour the wet mixture into the dry mixture and stir gently until just combined; avoid over-mixing to keep the cobbler topping tender.
Assemble the cobbler: Pour the batter over the cherry filling, spreading it evenly. Sprinkle 1 tsp cinnamon on top if desired, adding a warm note to the dish.
Bake to perfection: Place the baking dish in the preheated oven and bake for 35-40 minutes, or until the topping is golden brown and a toothpick inserted comes out clean.
Cool and serve: Once baked, let the cobbler cool slightly before serving. It’s perfect served warm!