Midnight Moon Cookies

Ingredients

• 8 ounces bittersweet chocolate, melted
• 1 pound confectioners' sugar (4 1/2 cups)
• 1/3 cup boiling water, plus more as needed
• 1 ounce (2 tablespoons) unsalted butter, softened
• Vegetable oil, cooking spray
• 1 1/4 cups plus 2 tablespoons all-purpose flour
• 1 cup plus 2 tablespoons cake flour (not self-rising)
• 3/4 teaspoon baking powder
• 3/4 teaspoon coarse salt
• 4 ounces (1 stick) unsalted butter, softened
• 3/4 cup plus 2 tablespoons granulated sugar
• 2 large eggs, room temperature
• 1/2 teaspoon pure vanilla extract
• 1/2 cup whole milk
• 1/2 teaspoon pure vanilla extract
• Vegetable oil cooking spray

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