How long can you go without paying before you go to jail?
I plan to send my 2010 return in, and a week later 2011, and then 2012, and work out a payment plan.
After that Ill file an extension on my 2013 and be caught up.
Please don't ask these questions on a public website. You never know who is reading this. There is a presumption of willfulness if you fail to file returns for 3 or more years. If the IRS or anyone calls and asks you any questions about your taxes, just get their name and telephone number and tell them your representative will call them. You should immediately hire a tax lawyer to represent you and steer this from criminal into a civil only matter. It sounds like you are preparing your returns yourself. That is not a good idea because there is a higher chance of audit for the missed returns.
Please have your tax attorney arrange for a good tax preparer. Also, unless yo pay the tax in full, your 2013 extension will not be valid. You should get the information to your preparer to have the 2013 return filed by April 15.
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3 lawyers agree
Mr. Cappuccio is correct. I will add that the IRS, absent factors indicating fraud, tax evasion, offshore accounts or large sums, usually does not recommend criminal prosecution provided the taxpayer has made substantial efforts to be fully compliant with the tax code. File your returns, then work out a payment plan. Generally speaking, it is better to be represented in this type of situation.
2 lawyers agree
Your situation is not uncommon, but do not be misled into thinking you can handle it yourself. You are in a fairly serious position, and you have not handled it yourself before. Although you may well indeed file and arrange to pay, it would be foolish to delay consulting with a tax attorney.
This is not intended to be legal advice, and is general in nature.
You should be careful in the filing and consult and attorney prior to.
This answer is based on general legal principles only and is not intended to provide specific legal advice. This answer is for informational purposes only and does not constitute the formation of a lawyer-client relationship. Any reader of this answer should not make decisions based upon in without first directly consulting with an attorney