Step 1: Preheat your oven to 350°F (175°C). Lightly grease a 9×13 inch baking dish with non-stick cooking spray or butter.
Step 2: In a large mixing bowl, combine the well-drained crushed pineapple, softened cream cheese, 1/2 cup granulated sugar, 2 tablespoons all-purpose flour, vanilla extract, and a pinch of salt. Mix until well combined and smooth.
Step 3: Spread the pineapple cream cheese mixture evenly into the prepared baking dish.
Step 4: In a separate medium bowl, whisk together the 1 1/2 cups all-purpose flour, 1/2 cup granulated sugar, baking powder, and 1/4 teaspoon salt.
Step 5: Cut in the cold unsalted butter using a pastry blender, two knives, or your fingertips, until the mixture resembles coarse crumbs with pea-sized pieces of butter.
Step 6: Pour in the milk and mix gently until a soft, shaggy dough forms. Be careful not to overmix.
Step 7: Drop spoonfuls of the topping mixture evenly over the pineapple cream cheese filling in the baking dish. Sprinkle the top with 1-2 tablespoons of granulated sugar.
Step 8: Bake for 40-45 minutes, or until the topping is golden brown and the filling is bubbly. If the top browns too quickly, you can loosely tent it with aluminum foil.
Step 9: Remove the cobbler from the oven and let it cool on a wire rack for at least 15-20 minutes before serving. Serve warm with ice cream or whipped cream, if desired.