Whatever you are imagining, the reality is more boring and more hopeful. I have walked hundreds of non-filers back into the system over 32 years, and here is the pattern: the fear is the worst part, the path is standardized, and the people who come back voluntarily almost always end up fine. You are not the worst case I have seen. You are probably not the worst case I have seen this month.
Six Years, Usually
IRS policy generally requires six years of returns to restore compliance - not every year since you stopped. The exact count flexes with your facts, especially where the IRS has already filed substitute returns for you or specific years hold refunds or large balances. Filing more than required can create debt policy never demanded; filing fewer leaves you locked out of every resolution program. Getting the number right is the first decision, and it is a judgment call, not a guess.
The Records Problem Solves Itself
You do not need a decade of shoeboxes. The IRS keeps wage and income transcripts for each year - every W-2, 1099, mortgage statement, and broker report it received - and those transcripts are the skeleton of every late return. Bank statements and reasonable reconstruction fill in the business expenses. Two timing notes that matter: refund years file first, because refunds die three years after the due date and I have watched hesitation forfeit five figures of withholding; and substitute-return years get repaired fast, because every month of delay closes doors on those.
Then the Balance, Then the Peace
Compliance restored, whatever balance is real gets resolved through the normal exits - payment plan, offer, hardship status - with penalty abatement layered on, and penalties on non-filer cases are substantial and frequently vulnerable. On the question that keeps you up at night: voluntary compliance before the IRS comes asking is the strongest protection that exists, because walking in the front door is the opposite of what prosecutors look for. Bring me the years. We will get this off your back for good.