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Preheat oven to 425°F.
Place short ribs on a sheet pan, brush tops with olive oil, and sprinkle with 1½ Tbsp salt and 1½ tsp pepper.
Roast 20 minutes; remove from oven.
Reduce temperature to 325°F.
Meanwhile, heat ¼ cup olive oil in a large (12-inch) Dutch oven over medium heat.
Add leeks, celery, onions and carrots; cook over medium to medium-high heat 20 minutes, stirring occasionally.
Add garlic; cook 1 minute.
Add wine, bring to a boil, reduce heat to medium and simmer 10 minutes, until liquid is reduced.
Add stock, tomatoes, Guinness, thyme, 1 Tbsp salt and 1½ tsp pepper.
Add ribs to pot along with juices and seasonings from sheet pan.
Bring to a boil, cover, and cook in oven 1 hour.
Uncover and cook for 1 more hour, until meat is very tender.
Transfer short ribs to a plate with a slotted spoon; discard thyme bundle and any bones that have separated from meat.
Simmer sauce on stove for 20 minutes.
Skim some of fat off top; discard.
Return ribs to pot, heat 5 minutes, and taste for seasonings.
Serve hot in shallow bowls spooned over Creamy Blue Cheese Grits, with extra sauce on the side.
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