Q: If someone failed to report an entire source of income over 2 years. What’s the chance they will see prison time?
A: It is impossible to say without additional information. This is also something that should not be discussed in an open forum. You need to stop looking for answers here and contact a tax attorney where attorney client privilege will apply.
David Ostrove agrees with this answer
Unlikely, if you pay the taxes due and all penalties. (Or make a true attempt to cooperate in making restitution.)
Positive efforts to make up all underpayments very important.
If the matter has already been sent to IRS criminal division, contact person in charge, admit underpayment and make a verifiable offer to make restitution. Federal authorities believe very much in the "one bite of the apple" approach. If you sincerely want to make amends and work out repayment the Federal Authorities will usually work out a deal with you. But, keep your word. Do NOT lie.
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