Tax Evasion

What is the name of your state? Indiana

My boyfriend has not paid income taxes in 8 years. Is there any way he can throw himself on the mercy of the IRS and start some kind of payback program where they won't put him in jail? How hard does the IRS pursue people that haven't paid taxes (he doesn't really owe that much).

[abezon]

He should see a tax pro for help filing the old returns. He may not owe anything at all.

Your boyfriend will be okay as long as he doesn't file a tax return out of the blue without filing for all those years he missed. Filing now would be waving a red flag in front of a bull. It is true that he may not owe any tax, but if he suspects that he does, the penalties and interest will be outrageous and the IRS will act if the amount is worth their trouble. To avoid all that terror, when he gets ready to start filing, a bankruptcy will protect him and his assets when the time is right. A Chapter 13 will set aside all penalties and interest as unsecured debt, which means it is dischargeable. He will be responsible for priority one debt, which is the tax. Sometimes, if your circumstances fall under hardship, your attorney can renegotiate your tax burden under the auspices of the trustee and a willing IRS agent who only handles bankruptcy returns.

If you don't want to file bankruptcy for whatever reason, you can file an offer in compromise after you send in your returns for all those years in arears; you make an offer of what you can pay and see if they accept it. If they don't, then you can fall back on the bankruptcy course of action. The forms for filing an offer in compromise are available online for free from the IRS. Take a look at them and you'll see what's involved.