The other day I took a phone call from one of our business clients. His business provides insurance services to other businesses. He asked me a very simple question, "I have a business client who has a group health insurance plan for him and his employees, and he needs to know whether or not he can deduct these expenses."
It became pretty clear to both of us, that although it may have been an easy question for him to ask me, the answer to that question is a lot more involved. Thanks to the prevalent use of pass-through taxable entities (S-Corps, and Partnership returns), and changes to tax provisions, deducting health insurance as a business owner is not as easy as paying the insurance bill.
If this business owner has a traditional C-Corporation the corporation would be able to deduct the full amount of the health insurance expenses as long as they have a qualified plan in place that covers all employees (without discriminating in favor of Highly Compensated Employees, or the business owners, or their families).
If this business is instead a Schedule C business or a single member LLC (disregarded entity) the business would not be able to deduct the portion of health insurance purchased for the business owner and/or his family. The health insurance expense for his normal employees (other than himself and his family) would be deductible. However, the portion of the expenses paid for his personal health insurance coverage would be includable on the front page of the business owner's personal income tax return (1040). Therefore, the business owner would be allowed to deduct on his personal return, personal health insurance expenses (to the extent that his business has earnings in the current taxable year). If the business owner had a loss for that same year, he would not be allowed to take the deduction on the front page of his personal return, but would instead include the expense on Schedule A (to the extent that health expenses exceeded 7.5% of AGI).
If this business is instead a S-Corporation, and the business owner is a more than 2% owner, the preferred method for deducting this expense is to include the amount as a "Gross-up" of W-2 wages to the owner/shareholder. This method is a little more involved, but basically at the end of the day, the deductibility is treated similarly to Schedule C business owners.
In conclusion, thanks to many changes in the tax code in recent years, businesses and individuals should be aware of costs and opportunities associated with business tax decisions. If you have concerns regarding your business's specific tax items, it is important that you use a qualified tax representative.