Heat 1 1/2 tablespoons olive oil in a large skillet over medium heat until the oil shimmers.
Add 2 cloves garlic, minced, and 1/2 teaspoon red pepper flakes; cook, stirring, about 1 minute, until fragrant and the garlic just begins to soften (do not brown).
Add 1 tablespoon capers (drained and rinsed), 5 kalamata olives, roughly chopped, and 1/4 cup parsley or arugula, roughly chopped; cook, stirring occasionally, about 2 minutes.
Add the (1) 15 oz can diced tomatoes and 1 1/2 teaspoons kosher salt; stir to combine and bring the mixture to a simmer. Keep the heat at a gentle simmer—hot enough to poach eggs but not a vigorous rolling boil.
Use the back of a spoon to make two small wells in the sauce. Crack 2 large eggs, one into each well.
Sprinkle 2 tablespoons grated Parmesan cheese evenly over the eggs and sauce.
Partially cover the skillet with a lid and cook at a gentle simmer until the egg whites are set and the yolks are still runny, about 5 minutes (check at 4 minutes if you prefer runnier yolks).
Remove the pan from the heat, sprinkle a little more Parmesan if desired, and serve immediately with 2 slices of bread for dunking.