FWIW I think that behavior may be specific to the Giant Pacific octopus[1]. I'm not sure if other octopuses (octopi? octopodes?) behave the same way.
As far as my understanding goes, the octopuses that don't exhibit that behavior are the exception to the rule instead.
Maybe they would be a better candidate for uplift than dolphins then? We could start out by fixing their lifespans (apparently it's a surgically resolvable problem, see [0]), and seeing what happens.
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I think they just don’t have the opportunity to produce culture. Maybe they could be taught but it seems like generational learning would be extremely unlikely.
Edit: their situation has always struck me as very poetic and sad. If they are conscious their existence seems so lonely. But maybe that’s just my mammalian bias!