Your business entertainment tax deductions fall into one of two business categories for deduction. The first category requires that the entertainment take place in a business setting. The second category triggers a piggyback entertainment deduction for the non-business setting, such as golf or scuba diving. Once you know the two rules, you have clarity in knowing how to claim your tax deductions for business entertainment.

How much of a vehicle deduction do you want from your business-vehicle purchase? A lot? A little? Could lawmakers trip you up in your desires? Absolutely. There are big differences in what you can deduct, depending on whether you buy a pickup truck, SUV, or car. Further, the differences among the categories depend on the weight of the vehicles. You need to know what the differences are if you are going to get the vehicle deduction you want.

Last month we explained how an S corporation could rent the sole shareholder’s personal residence for 14 days or less, obtain a tax-deduction for rent, and create tax-free income for the shareholder. An enrolled agent raises six issues that he thinks could negate this free-rent strategy. Learn what the issues are and why the strategy works.

You may be leaving thousands and even tens of thousands of dollars in unclaimed tax deductions on the table if you traded in a vehicle you owned on the lease of a business vehicle. Here’s a look at why the money gets left on the table. It’s a simple matter of thinking that this was a trade. For tax purposes, it was not a trade. And that’s usually good for your pocketbook.

If you have workers who are paid on a 1099 as independent contractors, you need to avoid one fatal mistake. When you make this fatal mistake, you subject your worker employment classification to either the tax court’s common-law seven-factor test or the IRS’s 20-factor common-law test. Both of these tests are hard on the employer and often result in harsh reclassification of the 1099 independent contractors to W-2 employee status.

Is your last payment of payroll taxes in the hands of the IRS or in the hands of an embezzler? How would you know? There’s one easy way to know: simply use the IRS’s online service to check. But that’s a lot of trouble, so why bother? Because if the money has been stolen, you (1) are out the money and (2) have to pay that same amount to the IRS. If you have to pay twice, you are going to be furious. Don’t let this happen.

Are you treating your business entertainment correctly? For example, do you cut your deductions if the entertainment rubs against the lavish or extravagant rule? Are you cutting your entertainment expenses for the 50 percent rule? Learn why it’s easy to misunderstand the lavish or extravagant and 50 percent rules and how that could be hurting your business entertainment tax deductions.