Heat 2 tsp. olive oil in a medium-large sauté pan over medium-high heat. Add squash to pan; season with 1/4 tsp. salt and 1/2 tsp. pepper and cook for 1 1/2 minutes on each side until they begin to brown.
Add tomatoes and garlic. Stir and cook for 2 minutes or until tomatoes begin to soften.
Add brie cheese and 1/2 cup pasta cooking water. Stir for 1 minute until cheese is melted and becomes creamy. Add in basil, reserving 2 tbsp. for garnish, and cooked pasta; stir to combine.
Plate pasta and garnish with remaining basil. Serve immediately.