►Warm 2 tablespoons olive oil in a large pot over medium heat. Season pork shoulder generously with salt and pepper, then add pork to hot pan and sear all over, about 10 minutes per side. Transfer pork to a plate.
►Add onion to oil remaining in pot and cook over low heat, stirring occasionally, until softened, about 7 minutes. Add fennel seeds, garlic, and chopped herbs and cook until fragrant, another 2 to 3 minutes. Season with salt and pepper. Add red wine and tomatoes, scraping up any browned bits from bottom of pot.
►Add seared pork and vegetable broth and season mixture again with salt and pepper. Simmer gently for 2 hours, or until pork shreds easily.
>Transfer pork to cutting board or clean plate. Bring remaining liquid to a rapid boil and cook until reduced and thickened, about 20 minutes. Taste and adjust seasoning as necessary.
►Meanwhile, heat oven to 425°F. Arrange sliced ciabatta in a single layer on a rimmed baking sheet. Drizzle with remaining 1 tablespoon olive oil, season with salt and pepper, and bake until lightly toasted, 5 to 6 minutes.
►Shred pork with two forks and season to taste. Once sauce is thick and seasoned, stir shredded pork back in to reheat.
►Put toasted ciabatta in a large bowl and spoon pork ragu over top. Garnish with ricotta salata and serve immediately.