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Preheat the oven to 350 degrees F. Add ¼ cup unsalted butter to an 8 by 8 glass baking dish. Melt the butter. Be careful when pulling the dish out of the oven. If the butter is too hot, it can splatter.
To a small bowl, whisk together the sugar, cocoa powder, all-purpose flour, baking powder and salt. Add the milk, vanilla and sourdough discard. Whisk until completely combined. Add the chocolate chips and gently combine. This is the cobbler mixture. Set aside.
To a different small bowl, mix together the granulated sugar and cocoa powder. Prepare boiling water on the stove or in an electric kettle.
Take the pan out of the oven with the melted butter. Spoon the cobbler mixture into the hot pan. Spread the mixture so it's in an even layer in the pan. Pour the sugar/cocoa mixture on top of the cobbler in a layer covering the entire cobbler. Pour the boiling water on top of the entire cobbler.
Bake the cobbler at 350 degrees for 30-35 minutes until the top of the cobbler is puffed up and set. Remove from the oven and let cool for 5-10 minutes before serving warm with a scoop of ice cream. Enjoy!