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How to Avoid Jail Time for Tax Blunders

It’s easy to slip up on a tax return. An honest mistake could cost you a penalty; an intentional violation of the law is another matter. That could send you to prison.

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And when the government seeks jail time for tax cheats, it gets it nearly 90% of the time.  Most people got into trouble because they failed to report income from a cash business, property sales or foreign earnings. Many also intentionally claimed wrong deductions.

The best way to avoid trouble – besides not engaging in fraud  -  is to keep track of cash receipts and employers. That way you can prove your case if you’re audited. And ignorance isn’t a defense. For example, someone who doesn’t  get a Form 1099 from an employer still has to report the income that would have been on it.

Right now, the IRS is paying close attention to Americans with money in Swiss and other foreign bank accounts. The tax authority is looking over many of these cases with a fine-tooth comb because of the heightened attention to the issue of offshore tax evasion. But generally, in cases like these, common sense has come into play in the past. A person who reported a lot of income in the U.S. but failed to report on a small foreign account would not have been at risk criminally.

A consultant providing services to Wall Street firms recently came to George M. Clarke, a partner at law firm Miller Chevalier in Washington, D.C. Clarke, worried about not having reported $60,000 of income after a customer didn’t send a 1099. The IRS, says Clarke, will want to know if the misstep is the only one he made and what kind of accounting system he uses. This kind of situation is common and not likely to lead to jail.

By contrast, Robert E. McKenzie, an attorney in the Chicago law firm Arnstein & Lehr LLP, recently helped two clients plead guilty to skimming money from their plumbing business to the tune of more than $100,000 a year. Each of the men will spend ten months in jail. They had been cashing some checks at a local check cashing store where the IRS had a sting operation set up.

When the IRS asked his clients for their books, the men showed them records listing numerous checks –  but the IRS pulled out its own list of those cashed at the local store, McKenzie recounts, and asked “What about these?”

Advisers face their own set of rules and can also go to jail. Chicago tax lawyer Paul Daugerdas has been on trial in New York City in recent days over his role in selling tax shelters and advice to wealthy clients. For the government, putting an adviser behind bars is a great deterrent, saving it from having to lock up every client he might have had in the future.

Readers, have you ever unintentionally made a mistake on your taxes that you worried would trigger an IRS investigation?


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About The Tax Blog

  • The Tax Blog brings together a team of award-winning tax journalists from the Dow Jones network and around the web to examine the tax issues, changes and legislation that affect families, investors and small business owners. Our contributors include Tax Report columnist Laura Saunders (WSJ), Tax Guy columnist Bill Bischoff and senior reporter Jilian Mincer (, retirement-focused reporter Anne Tergesen (WSJ), wealth management writer Arden Dale (Dow Jones Newswires), TaxWatch columnist Eva Rosenberg and personal finance reporter Andrea Coombes (MarketWatch), and reporter Alyssa Abkowitz (SmartMoney). They’ll provide the latest news and insight, mine the tax code for tips and loopholes, and answer your questions about tricky tax situations. Contact the The Tax Blog with ideas, suggestions or tax questions at