Step 1

Heat oven to 325°. Pat lamb dry; season with salt and pepper. Heat oil in a Dutch oven or other large heavy pot over medium-high heat. Cook lamb, turning occasionally, until browned on all sides, 6–8 minutes; transfer to a plate.

Step 2

Add fennel, onion, and garlic to same pot and cook, stirring frequently, until golden brown and softened, 6–8 minutes. Add wine and bring to a boil, scraping up brown bits. Reduce heat and simmer until reduced by half, 6–8 minutes.

Step 3

Add orange, bay leaves, cinnamon stick, tomatoes, and broth along with lamb to pot. Bring to a simmer, cover pot, and transfer to oven. Braise until lamb is fork-tender, 1½–2 hours. Transfer lamb to a clean plate.

Step 4

Strain cooking liquid through a fine-mesh sieve into a large bowl; return to pot. Bring to a boil, reduce heat, and simmer until thick and velvety, 20–30 minutes.

Step 5

Stir in pomegranate molasses, if using, and return lamb to pot and cook, stirring to coat, until heated through. Serve lamb with Cucumber-Dill Tzatziki, Three-Herb and Red Onion Salad, and Westward Pita Bread.