Cook the pasta in a large pot of boiling, salted water until just al dente, then drain and set aside.
In a large skillet, heat the olive oil over medium heat until shimmering, filling your kitchen with a subtle, fruity aroma.
Add the minced garlic and red chili flakes to the skillet, cooking for about 30 seconds until fragrant — listen for a gentle sizzle and watch the garlic turn slightly golden.
Stir in the diced tomatoes with their juice, breaking up the tomatoes slightly with your spoon, and let the sauce simmer for 5 minutes until it thickens just a bit and deepens in color.
Add the sliced black olives and capers to the sauce, stirring to combine. The mixture should look briny and flavorful, with a slightly chunky texture.
Increase the heat to medium-high and add the calamari rings directly into the sauce, spreading them out evenly in the pan.
Cook for about 2-3 minutes, gently stirring, until the calamari just turns opaque and firm, smelling salty and seafood-like, but avoid overcooking to keep it tender.
Season with salt and freshly ground black pepper to taste, adjusting the heat as needed to maintain a gentle simmer.
Combine the cooked pasta with the calamari puttanesca sauce, tossing gently to coat all the strands evenly, and heat together for a minute or two so flavors meld.
Observe the final dish: the pasta glistens with the vibrant, spicy sauce, and the calamari lends a slight chew that contrasts beautifully with the silky tomato mixture.
Serve immediately, garnished with a sprinkle of fresh herbs if desired, and enjoy the lively, ocean-inspired flavors.
