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I'm worried that the IRS will audit him, or will figure out that he's not paying taxes and come after him. If they do, what happens? He makes about $20,000 a year. Can they fine him? Can they put him in jail?
I'm no expert, but anyone who earns more than $700 per year is required to file a tax return. Deliberately not filing a tax return is called tax evasion, and he could be fined or jailed or both depending on the amount involved and the mood of the IRS and prosecutor. Truthfully, for 20 grand a year your boyfriend isn't in the same league as 20 mil a year drug dealers or mobsters so the IRS has little reason to come looking. But if something else they're investigating dumps info right in their lap (like auditing the 'employer' which pays him under the table), they will use the information.
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Also: he's considering switching jobs. He'd probably start paying taxes at his new job. If he *starts* paying taxes, will that tip the IRS off? Is there a statute of limitations--after a year or three years or five years, if they don't catch him, is he safe?
If anything, this would probably make an IRS investigation less likely, providing that nothing on his tax return is controversial. Typically there is a 3 year limit to investigating past years, however this can extend to 7 years under certain circumstances like suspected tax fraud or other stuff carrying major charges and penalties.