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Heat a large pot or Dutch oven over medium heat and add 2 tablespoons of olive oil.
Once oil is shimmering, add 1 cup chopped yellow onion, 1 cup chopped carrots, and 1 cup chopped celery; sauté, stirring occasionally, until vegetables are tender and fragrant, about 5–7 minutes.
Stir in 3 cloves minced garlic and 1 teaspoon dried oregano; cook until garlic is fragrant, about 1 minute.
Pour in 28 oz diced tomatoes (undrained) and 6 cups vegetable broth; stir to combine and bring to a boil.
Reduce heat to medium–low, cover, and simmer for 10 minutes to meld flavors.
Add 1 cup dry ditalini pasta, cook uncovered until pasta is al dente, about 8–10 minutes, stirring occasionally to prevent sticking.
Stir in 5 oz fresh spinach and let wilt into the hot soup for 1–2 minutes.
Season with 1 teaspoon salt and ½ teaspoon black pepper (or to taste); taste and adjust seasoning as needed.
Ladle soup into bowls and serve hot, optionally topped with grated Parmesan cheese and served with crusty bread for dipping.