In a medium bowl, add canned whole peeled tomatoes and crush, using your hands, until broken down but still a little chunky.
Heat olive oil in a large cast iron skillet over medium high heat. Add cherry tomatoes, garlic, red pepper flakes and Italian seasoning until garlic is golden, about 1-2 minutes.
Stir in crushed tomatoes with all the juices; season with salt and pepper, to taste. Bring to boil; reduce heat and simmer, stirring occasionally, until just thickened, about 10 minutes.
Stir in spinach until wilted, about 1-2 minutes.
Remove from heat. Using the back of a wooden spoon, make 2-inch wells in the sauce, immediately cracking the eggs gently into each of the wells. Season eggs with salt and pepper, to taste.
Heat skillet over medium low heat. Cover and cook until eggs are just set, about 4-5 minutes.
Serve immediately with fresh herbs and crusty bread.