Preheat your oven to 375°F (190°C). Lightly grease a 9x13 inch baking dish.

In a large mixing bowl, combine the undrained crushed pineapple, 1/2 cup granulated sugar, cornstarch, melted butter, vanilla extract, and a pinch of salt. Whisk until all ingredients are well combined.

Pour the pineapple mixture evenly into the prepared baking dish.

In a medium mixing bowl, whisk together the flour, 1/2 cup granulated sugar, baking powder, and 1/2 teaspoon salt.

Add the cold, cubed butter to the dry ingredients. Use a pastry blender or two forks to cut the butter into the flour mixture until it resembles coarse crumbs.

Pour in the milk and stir gently with a fork until just combined. Be careful not to overmix; a few small lumps are perfectly fine.

Drop spoonfuls of the cobbler topping over the pineapple filling, spreading it out to cover as much of the fruit as possible. It does not need to be perfectly uniform.

In a small bowl, mix the 1 tablespoon granulated sugar with 1/2 teaspoon ground cinnamon. Sprinkle this mixture evenly over the cobbler topping.

Bake for 35-45 minutes, or until the topping is golden brown and the pineapple filling is bubbly around the edges. If the topping starts to brown too quickly, you can loosely tent it with aluminum foil during the last 10-15 minutes of baking.

Let the cobbler cool for 10-15 minutes before serving to allow the filling to set slightly.

Serve warm, plain or with a scoop of vanilla ice cream or whipped cream for an extra treat.