A few years ago, I got in trouble with the IRS for failing to forward my payroll taxes for one quarter. Times are tight, and I dropped the ball again for another quarter this year. Now, the IRS revenue officer assigned to my case is refusing to cut me a break. What can I do?

Are you familiar with the expression “Fool me once, shame on you; fool me twice, shame on me”? The first time you failed to forward your payroll taxes, the IRS revenue officer probably recognized you made a bad decision in a tough spot, and allowed you to get away with repaying your debt in full (perhaps with accompanying interest and penalties). But, now that you’ve pulled this trick a second time, the government may be inclined to stick you and your company in the “habitual offender” file. As a result, you will be treated much less leniently.

Is this fair? Probably not. The worst payroll offenders are presidents and CEOs who continue to “pyramid” their payroll deductions quarter after quarter, year after year, resulting in a pool of cash they use to invest in their business (or, as is more often the case, use to fund their own lavish lifestyles).

Since, by your own account, you only failed to forward your payroll taxes to keep from going bankrupt and throwing your workers onto the unemployment line, you may feel like you are entitled to some “brownie points” compared to these hardcore felons. But, that won’t necessarily be the conclusion of your new revenue officer, who will reasonably claim you should have learned your lesson on the first go-round.

What can you do in this sticky situation? A good first step is to hire an experienced Oklahoma tax expert from the law firm of Travis W. Watkins, PC (800-721-7054). We’ll take up the cudgels on your behalf, and deal directly with your revenue officer to obtain the best possible outcome for your case.