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Calamari has to be cooked quickly or for a long time. We usually let it simmer in the red sauce for about 2 hours... Sometimes we let it keep going if we are still cooking other things and it stays perfectly tender.
I prefer to cook it quickly. . . otherwise it has the tendency to get tough and chewy. Here is my recipe for cooking squid in a red sauce with the addition of mussels. I make this for my family every year for Christmas Eve dinner. http://www.food52.com/recipes...
The usual rule for squid is less than 3 minutes or more than 3 hours. Anything in-between will turn it into rubber.
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If your frying or grilling, no more than 3 minutes. If you're cooking it in gravy, I would opt for the 3 hours. It won't be rubbery.
I've been known to really take my time - the real question here is squid quality. For a tougher squid you really need to break down some off that fibrous quality by cooking it for what seems like 6 months - don't get me wrong, I've been known to fry up a squid in minutes...really just depends. Either way - you need to experiment. No two batches of squid are the same...find your own way to tae it down.
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