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Step 1
Brown oxtails. Generously season oxtails on all sides with salt and pepper.Heat oil in a large heavy-bottomed pot over medium-high heat. Once shimmering, add oxtails (you might have to do this in batches depending on the size of your pot). Cook until browned on all sides, about 8 minutes total, then transfer to a plate.
Step 2
Saute vegetables. Add onion, celery and carrot to the pot and season with salt and pepper. Cook until just tender, about 5 minutes. Add garlic and cook 1 minute more. Add oregano and bay leaves then add back the oxtail and any remaining juices on the plate.
Step 3
Simmer. Add the water and bring to a boil, then reduce the heat to a simmer, cover and cook until oxtail is tender, about 1 hour.
Step 4
Add barley. When a sharp knife easily slips into the oxtails add the barley to the soup. Cover and cook for an additional 30 minutes.
Step 5
Serve. Season with salt and pepper and remove oregano sprigs and bay leaves then ladle soup into bowls. Serve with a generous dollop of chimichurri on top.