On assessment tests where he doesn't have to "show his work" or write anything he surpasses them. Math problems that are on the "intense" level he masters but struggles with "easier" items. The harder the problem, the better he does.
This describes more than a handful of people I've known. It seems the new/difficult aspects engage a different part of the brain which is not utilized for routine tasks.
I don't understand how he can do so well on really intricate and thought provoking details, but then if he has to "show" his work he completely butchers it and gets the problem wrong. If he has a really tough word problem, he can do the problem in his head. But then if you ask him to take that word problem and write it down as a "formula" he can't. Does anybody understand this?
It seems these may be different skills. By analogy, a person can pick up a pencil almost without thinking consciously about it but if asked to explain step by step how they did it, which internal muscles they used, it would be difficult.
What do we do at this point?
Is it possible for him to write his answers, then go back to "check his work"? In reviewing his work, it may be possible for him to slow down the computations to a one step at a time, and basically write out his thinking as he "checks his work".