To help tenderize, pound the calamari gently a few times on each side using a kitchen mallet or a heavy skillet (be careful not to tear the flesh).
Cut the calamari into ½ inch thick rings. Pat dry with a paper towel. Make sure they are dry or you risk that they will be more soggy than crispy.
In a large bowl add the breadcrumbs and season with salt and pepper. In a separate bowl add the olive oil. Quickly dip the calamari rings in the oil and shake off excess. Toss the calamari rings into the breadcrumb mixture; gently pressing to coat. Lay the prepared calamari on a baking sheet or cutting board lined with parchment paper as you finish preparing the batch.
Preheat the air fryer oven to 400° degrees F. Lightly grease the basket of the air fryer with oil (or line it with tinfoil and spray). Place the calamari rings in a basket, in a single layer. Do not overcrowd the basket, or they won't crisp properly. Cook in multiple batches if needed.
Cook the calamari for 8-10 minutes, flipping them halfway through cooking.
Transfer the calamari to a plate and immediately season with a sprinkle of salt. Repeat the steps above with the remaining calamari. Eat the calamari immediately with some lemon wedges and dipping sauce (if desired).