Pre-heat oven to 200C. Brush squash and bell pepper (cut into strips lengthwise) with olive oil, season with salt and pepper and bake until squash is soft and pepper is roasted, about an hour. You might have to remove the peppers from the oven before the squash.
In the meantime, prepare the dough gathering flour, eggs and squid ink in a food processor and working it in impulses until you get a medium cous-cous texture. Pour the mixture onto floured counter and knead until you get a smooth feeling ball. Wrap in kitchen wrap and rest for about 30 minutes at room temperature. Then roll the dough and cut the tagliolini.
In a large skillet heat up oil on medium heat, with minced garlic and shallot, cooking for about a minute, without browning. Add calamari rings and halved tomatoes, salt and pepper, sprinkle with wine and briefly cook on medium-high heat, just enough to cook the calamari. Add the minced parsley and mix. Remove the calamari from the skillet and reserve, keeping the sauce on the stove until reduced.
Remove from stove and put the calamari back in the skillet.
Cut the roasted bell pepper in chunks and add to the sauce.
In a deep cup put the peeled cooked squash, the pepper flakes, a little olive oil and some rosemary leaves (about a teaspoon). Blend with a hand blender until smooth. Adjust salt and pepper, then strain and reserve.
Boil your tagliolini in salted water (about 3 minutes), drain and add to the skillet with the condiment.
Plate with a spoonful of squash sauce on the side, a nest of tagliolini on the other and garnishing with more sauce, fresh parsley and some olive oil. Serve immediately.