He explained that he knows *how* to ask for help (i.e. what words to use) but not *when* he needs help. How can he not understand this?
Possibly he has been compensating for a long while, and has grown used to skipping things and guessing as strategies which are often successful? You may wish to consider talking with him about these strategies (which he may not immediately recognize if they have become ingrained/automatic), and helping him recognize them as a signal that another strategy could be employed: asking for clarification. A helpful teacher who "gets it" may spend the time to discuss his guesses while also providing clarification of the instructions/directions in other words/phrases until he has the aha moment and all the puzzle pieces seem to fit.
