Will the IRS cut a deal with me if I have unfiled returns?
Regularly, I get clients in my office who have not filed returns for many years. You may be inclined not to file if you have gone long periods (decades even) without filing returns. You must file your returns. First of all, non-filers are considered criminals by the IRS, and you can get up to a year in jail for this misdemeanor. The IRS has pushed in recent years to make this crime a felony. Second, more often that not, the painstakingly slow IRS will ultimately uncover your non-filings. Third-Parties are constantly filing information about your income (1099's for example), so that they are not left holding the bag for your taxes. Bottom line, it is simply not worth the risk to avoid filing.