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Combine cherries, onion, sherry, water, bay leaf, and a half teaspoon each salt and pepper in a small saucepan over medium high. Bring to a boil, lower to a simmer and cook until thickened and cherries have started to break down, about 20 minutes.
Meanwhile, whisk together flour, 2 tsp pepper and 1 tsp salt in a large bowl. Pat quail dry and toss in flour mixture to coat completely. Heat 1 inch of oil in a large, deep skillet over medium high to 350°F. Add quail and cook until golden brown and cooked through, flipping as needed for even cooking, about 10 minutes total. Remove from the skillet to a paper towel-lined plate and keep warm.
Place broccoli rabe and 1/4 c water in a medium non-stick skillet with a lid over medium heat. Cover and cook until broccoli rabe is tender and bright green, about 5 minutes. Remove the lid and if there is any remaining water, continue to cook until almost all remaining water has evaporated. Add olive oil and remaining 1/2 tsp each salt and pepper. Cook, stirring often until broccoli rabe begins to char, about 5 minutes. Serve alongside quail and drizzled with cherry sauce.
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Looking forward to making this for dinner.