M.R.
S.,
What you are describing is Autistic logic. He will always have trouble with generalization issues, he can apply a concept to the novel way it was taught, and it will take a great deal of time for him to learn to then apply that to something else. It does not mean that he is not learning. Ask your childs teacher about this, and if he has a continuing issue with generalization, you may want to address this with an IEP goal, most probably in his speech IEP. I bet, if you look at his evaluation, and you look at his IEP, this is addressed, but you just have not ever thought about the reality of AS in this way.
You will be dealing with generalization issues for a very long time...I know this is frustrating, and not what you want to hear. Keep plugging away. You have the expectation that he will make progress with his IEP, but there are some realities that cannot be overcome so easily. What you want to be sure that you have is measurable goals, goals that are reasonably calcuated for him to make progress. It is likely that you could do better with his IEP goals (most only have the appearance of measurablity.) My adivice is that you go to www.wrightslaw.com and read about smart IEP goals, read the article "Tests and Measurments for Parents and Advocates" and start off on this early road to getting what your child needs from the IEP, based on numbers you understand and can use to request measurable, meaningful IEP goals that get your son to the place you want him to be (within a reasonable margin, given his challenges.)
M.