Preheat the oven to 400°F (200°C). Cut tomatoes in half and place on a baking sheet. Drizzle with olive oil, salt, and pepper. Roast for 25-30 minutes.

In a saucepan, sauté chopped onion and minced garlic until translucent. Add roasted tomatoes and vegetable broth. Simmer for 10 minutes.

Blend the soup until smooth and adjust seasoning if necessary.

Bake potatoes until tender. Let cool, then scoop out the insides into a bowl.

Mix scooped potato with cheddar cheese, sour cream, milk, and chives. Spoon mixture back into potato skins.

Place filled potatoes back in the oven and bake for an additional 15 minutes until cheese is melted.