Pork Shoulder Roast with Tomatoes

Preheat oven to 350 degrees. Season pork with salt and pepper. In a large Dutch oven or other heavy pot, heat 1 tablespoon oil over medium-high. Add pork, fat side down, and cook, turning until browned on all sides, 8 minutes. Transfer pork to a plate. Pour off fat, return pot to medium-high, and add remaining tablespoon oil. Add onion; cook until translucent, 5 minutes. Add garlic; cook until fragrant, 30 seconds. Add tomatoes; season with salt and pepper. Add broth and vinegar and cook, stirring and scraping up browned bits. Return pork to pot with juices; sprinkle with paprika.

Bring mixture to a boil over high. Cover, transfer to oven, and cook 1 hour. Remove from oven; with tongs, flip pork. Return to oven and cook, uncovered, until tender, 1 hour, basting pork with juices every 15 minutes. Transfer pork to a cutting board; let rest 15 minutes. Slice pork and serve with sauce.