I was also under the impression that he was very close to citizenship last year in May or June. I'd assume that there were several major mistakes along the way. Maybe he thought that merely residing in the country for seven or eight years, as he has, while having a green card, brought citizenship?
"Specifically, you must show that you:
are a lawful permanent resident (LPR); that is, you have a green card
have, as an LPR (or "conditional resident"), resided "continuously" in the U.S. for at least three years (if married to and living with a U.S. citizen all that time), or five years
have been actually, physically in the U.S. for at least half the required three or five years before filing your application
have resided continuously for three months in the state where you filed your application for naturalization, and
have not abandoned your residence in the United States.
Requirement of LPR Status
Having status as an LPR basically means having a green card. It comes with the right to live and work in the U.S. on a permanent basis, so long as you don't do anything that makes you deportable, such as committing a serious crime. Conditional residence also counts (for example, if you got your green card based on a relatively new marriage to a U.S. citizen, and had to go through a two-year testing period), so long as you converted to permanent residence at the end of that time.
When you file your naturalization application with U.S. Citizenship and Immigration Services (USCIS), you'll be asked to provide a copy of your green card to prove your LPR status.
Requirement of Continuous Residence in United States
"Continuous residence" is a legal term within U.S. immigration law. The word "residence" means where you actually live, that is, your dwelling or home. Residence "in the U.S." can include living in any of the 50 states or U.S. territories (Guam, Puerto Rico, or the U.S. Virgin Islands).
Unless you're married to a U.S. citizen, you have to reside continuously in the U.S. for five years after you become a LPR before you're eligible for naturalization.
But some immigrants are credited with time before they actually held their green card. Refugees can count all the time since entering the U.S. as though they were LPRs, so long as they received a green card before applying for naturalization. Asylees can count one year of their time before green card approval (in fact, their green cards will show that extra year; it will be backdated one year from the actual approval date)."
He's met all the requirements except clearly paperwork requirements. Who was advising him? Did he not apply to be a lawful permanent resident?