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It seems to me like a child who is desperate for attention and will act 'dumb' to get it.
I think I'd continue the time outs with ignoring him, but then make sure he gets your attention in a positive way when he does complete the task. He sounds like he wants the attention but doesn't know how to get it in a positive way.
Make sure he's getting tons of positive attention when he does anything correctly and in a timely manner. He may have had to get attention by acting helpless in his previous situation and may have just been ignored when he did things right.
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