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Melt chocolate in a double boiler over barely simmering water or microwave on Medium until just melted.
Whisk flour, cocoa, baking powder and salt in a medium bowl. Beat butter, oil and brown sugar in a mixing bowl with an electric mixer on high speed, scraping down the sides once or twice, until light and fluffy. Add eggs and vanilla and beat until well combined. Stir in the melted chocolate. With the mixer on low, alternate adding the dry ingredients and milk, starting and ending with the dry ingredients. Cover and refrigerate until chilled, at least 1 hour and up to 8 hours.
Preheat oven to 350°F. Line a large baking sheet with parchment paper or a nonstick baking mat.
Place confectioners’ sugar in a shallow bowl. Roll the dough into 1-inch balls (about 1 tablespoon each). Roll each ball in the sugar to coat. Place the cookies 2 inches apart on the prepared baking sheet. Refrigerate the remaining dough between batches.
Bake the cookies until the sugar splits, about 12 minutes. Transfer to a wire rack to cool. Repeat with the remaining dough.