He has been a permanent resident well over 5 years now so that part shouldn't be an issue. So basically our best option right now is get my wife's application in ASAP and hope we get lucky and if not proceed from there. We should have started the naturalization process sooner but ROC took forever and I was unaware that I could start naturalization in the middle of that process. Then after ROC we kind of put it off because we were in a tough financial situation for a while. I was not aware until recently that my wife had to be naturalized before my step son turned 18 in order for him to derive citizenship from her or we would have made this a higher priority.