The danger of rubberiness when cooking cuttlefish or squid is well known. The secret of avoiding this tragedy is either to cook them fast and short, for just a few minutes, or long and slow, for at least 1 1/2 hours. This dish can be done either way. The fast option is to cook the sauce without the cuttlefish, then flash-fry the cuttlefish and add it at the end

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Note added at 1 hr (2008-10-31 09:29:14 GMT)
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Cuttlefish, like squid, must be cooked in either one of two ways: In a ragingly hot pan for 2-3 minutes, or stewed for the better part of two hours.

The reason for this is because the muscles of cuttlefish, squid and octopus are very dense, with enormous amounts of connective tissue -- remember they have no bones and can move in all directions, meaning these critters need extremely fine motor control of those little arms.

Flash fry the legs and body (which is typically cut into rings) and you haven't let that connective tissue harden up. Stew it for hours and you've broken that connective tissue down.

http://fishcooking.about.com/od/meetyourfish/p/cuttlefish_pr...

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Note added at 1 hr (2008-10-31 09:32:37 GMT)
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Flash fry the cuttlefish until they’re golden brown, then remove them from the wok. Add all the vegetables and stir fry for 3 or 4 minutes, add the soy sauce and the prawns. Return the cuttlefish and continue to stir for another minute.
http://andrewkbrown.wordpress.com/2007/04/02/stir-fry-with-p...

Cuttlefish
Hugh says:
Sustainable and plentiful UK catch.
Avoid mess - ask the fishmonger to prepare it.
Either flash fry or stew gently until tender.
http://www.channel4.com/food/features/eat-ethically/plenty-m...