In a large pot or deep skillet, heat a drizzle of olive oil over medium heat. Add the diced onion and sauté until translucent, about 3-4 minutes.
Stir in the minced garlic and cook for another minute until fragrant.
Add the halved cherry tomatoes, dried oregano, and red pepper flakes (if using) to the pot. Cook for about 3-5 minutes, allowing the tomatoes to start breaking down.
Pour in the vegetable broth and bring to a simmer.
Add the penne pasta to the pot, stirring well to combine. Cook for 9-11 minutes, stirring occasionally until the pasta is cooked al dente and the liquid has reduced, leaving a creamy sauce consistency.
Lower the heat and stir in the heavy cream and chopped basil. Season with salt and pepper to taste, adjusting the seasoning as desired.
Remove from heat and let it sit for a couple of minutes to thicken slightly before serving.
Serve warm, garnished with a sprinkle of grated Parmesan cheese and a few extra basil leaves for a fresh touch.
Notes
Feel free to adjust the spice level by adding more or less red pepper flakes.