Heat 1 tablespoon olive oil in a skillet over medium heat. Cook and stir onion and red pepper with a pinch of salt in hot oil until onion is soft and translucent, 5 to 7 minutes. Remove from heat and cool to room temperature.

Stir sausage, minced tentacles, onion mixture, parsley, egg, smoked paprika, salt, and pepper together in a bowl until evenly combined. Transfer mixture to a piping bag.

Pipe sausage mixture into tubes, filling about each tube about 2/3 full. Thread a toothpick through the top of each tube to fasten the opening together. Place stuffed tubes on a plate, cover the plate with plastic wrap, and refrigerate until completely chilled, about 1 hour.

Preheat an outdoor grill for medium-high heat and lightly oil the grate.

Brush tubes with remaining olive oil to coat on all sides and season with salt.

Cook stuffed calamari on the preheated grill, turning occasionally, until stuffing is cooked through, 10 to 12 minutes. An instant-read thermometer inserted into the center should read at least 155 degrees F (68 degrees C).