5. Preemptive strikes work. If you have an unusually large deduction to report -- a big medical expense or a large one-time charity donation -- it will attract the eyes of the IRS. Don’t give it the chance to question you. Instead, attach a disclosure Form 8275 or documentation explaining the reason for this deduction. If you are willing to explain and provide documentation up front, then the IRS may have its curiosity sated.
6. Keep notes, save receipts and get organized. If you are itemizing your deductions, good records are crucial. Having a paper trail is the best defense should you get audited. Make sure all of your reported deductions are legitimate and that you have back-up receipts for everything. I drop all of my receipts and tax information into one box all year and then, when it is time to prepare, I have all my records in one place -- no searching around the house or waiting for credit card companies and banks to send duplicate copies of missing data.
7. Beware of the pitfalls of certain jobs. Face it. If you are self-employed or have a job that traditionally pays in cash, you are more likely to be audited. Those who must attach a Schedule C to their taxes are three times as likely to be audited – and those in certain professions, like cab drivers and waiters, or those who work from home (and deduct their home office), are also under closer scrutiny by the IRS. Short of changing your type of employment, there is nothing you can do about it – except make absolutely sure you follow Rule #1 (“come clean”) and Rule #6 (“keep notes, save receipts and get organized”).
8. Make timely and accurate estimated tax payments. Remember to make your quarterly estimated tax payments and don’t underestimate the amounts. Neglecting to make payments or underestimating the amount you owe will attract IRS attention. It may cost a little more today to overpay on those estimates -- but it is worth it. If you underestimate what you owe in the current year in question, this could result not only in interest that you will owe, but also penalties