OP, in terms of timing, our son took the SSAT in December last year. He was in a terribly hot room sitting on a science lab stool hunched over (he is big), and he did not do well; we were not sure if it was the test or the circumstances. He wanted to take them again. He did so in January and did much better . So I would have your son take them the first time in November, which gives him two more testing dates if he doesn't do as well as he/you would like. Good luck. It is a stressful process, but my experience is that kids coming out of K-8 schools really end up in the right places for them, which is a great thing!