In a clean bowl, stir together the strawberries and 1/8 cup of brown sugar. Set aside to macerate.
Add the butter to an 8x8-inch baking dish and place in the preheated oven until the butter is melted.
Meanwhile in a bowl or glass measuring cup, whisk together the remaining 1/2 cup of brown sugar with the vanilla and milk. In a separate large bowl, whisk together the flour, baking powder, cinnamon and salt. Pour the wet ingredients into the bowl with the dry ingredients. Use a spatula to stir until a smooth batter forms.
Carefully remove the baking dish from the oven and pour the batter over the melted butter. Use a knife to swirl the batter and melted butter together so the butter isn't all pooling at the edges.
Drain the strawberries. Carefully spoon the strawberries over top of the cobbler.
Bake for 45-50 minutes or until the batter is golden brown and the strawberry juices are bubbling. Serve warm with vanilla ice cream.