Preheat oven to 450℉. Rinse tomatoes and pat dry. Peel garlic cloves. On a baking sheet lined with parchment paper, toss tomatoes and garlic in olive oil. Season with a few sprinkles of salt & pepper. Bake in oven for about 30 minutes, until tomatoes are bursting.
While the tomatoes cook, boil pasta until al dente according to the package.
Once tomatoes are bursting, remove from oven and let cool down for 8-10 minutes. When tomatoes and garlic are no longer steaming, add to a high-power blender/food processor. Add in sundried tomatoes, milk, oregano, and chili flakes. Blend until smooth.
Add pasta and sauce back to pan and stir until combined. Serve topped with grated parmesan and parsley.