In a large skillet, heat the olive oil over medium heat. Once hot, add the minced garlic and sauté for about 30 seconds, or until fragrant. Be careful not to burn the garlic, as it can turn bitter.
Stir in the red pepper flakes, capers, and chopped kalamata olives. Cook for another minute, allowing the flavors to meld.
Pour in the can of diced tomatoes along with the kosher salt. Stir well to combine, then bring the mixture to a gentle simmer. Let it cook for about 5-7 minutes, so the sauce thickens slightly.
Create small wells in the sauce using the back of a spoon. Crack the eggs into these wells, cover the skillet, and let the eggs poach for about 5 minutes, or until the whites are set and the yolks are still runny.
Once the eggs are cooked to your liking, sprinkle the grated parmesan cheese over the top and add the chopped parsley or arugula for a pop of color. Serve the Puttanesca Poached Eggs with slices of your favorite bread for dipping.