Place a rack in center of oven; preheat to 350°F. Mist a 9-inch square glass baking dish with cooking spray. Stir cherries, 2 Tbsp. sugar, kirsch and juice in baking dish to combine. Roast until bubbly and juices have thickened, about 15 minutes. Transfer to a bowl and let cool completely.
Mix cocoa and 1/4 cup sugar in a bowl. Whisk in coffee until sugar and cocoa have dissolved. Let stand for 5 minutes. Stir in milk and extracts; pour into another 9-inch square baking dish. Freeze until completely frozen, about 1 hour, scraping frozen crystals from edge of pan with a fork every 15 minutes.
When ready to serve, scrape granita into chilled glasses, breaking up any large pieces with a fork. Top with cherries.
This dessert is absolutely delicious! But the directions for the granita are misleading. Per most granitas, you should freeze the mixture for an hour first, then keep it in the freezer, scraping every 30 minutes, for another 3 hours or so. Otherwise, the consistency just is not right at all.
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