I guess for us we decided that any decision we make is not a permanent one, and pretty much any desicion we could make in our public school setting would not be perfect. My son was "fine" with his school situation because he is a very social person but in the 2 years he'd been in school I saw huge changes in him.. I was already seeing him get lazy about anything "work" related because it was so boring and he became less mature rather than more mature. For these reasons we decided giving him the nudge to grade skip was a good idea even though he was apprehensive about leaving his "friends" (who he never interacted with outside of school and mostly just bossed around). After the first day of his skip he was asking to go back and after only 2 weeks I have seen the old him returning. He is so happy, loves the work (which is still easy but a closer match), and is acting more mature... My gut feeling was that this is where he belonged and so far it's been nothing but amazing. Our public schools do not have good options for differentiation. Everything is focused on standardized testing so anything he did at his level would be extra work on top of being in a boring school situation at least for the next 4 years. I wasn't about to waste 4 years of my child's life sitting in a classroom learning how to deal with being bored. I like to think that I am raising my kids to be independent and adaptable so although I know this is the right choice now, I also know it may change later. If he finds his social situation too difficult as he gets older, we will address that when it happens and adjust, whether it means pulling him out for a year or moving to a new school district or whatever... You really have to look at your sons personality individually. Since your son is much older than mine, I think you can also weigh his feelings more heavily, although ultimately my opinion is that what most of us are striving for here are kids that will learn the necessary skills to be successful and happy in life with their abilities and it's our job as the parents to make the final decisions on what will help them do that the best. Definitely talk to him about it and think about whether you feel he is missing something valuable by not skipping. I know my son was missing out by being held back, at least at this point in his life. All of the things in that article "What a Child Does not Learn" are important to me and my family and my child was definitely not learning those skills. Good luck!