Premiums for Medicare health insurance can add up to a substantial sum. That’s especially true if:

• you have a high income, and
• you’re married and both you and your spouse are paying premiums.

Fortunately, the premiums can potentially help your tax situation. The dollar benefit of Medicare tax deductions depends greatly on where you can deduct the premiums:

• The business deduction produces the maximum tax benefit.
• The self-employed health insurance deduction on line 29 of Schedule 1 of your Form 1040 produces the second-best benefit.
• The itemized deduction is either useless or produces the third-best benefit.

Number 1: The Business DeductionYou flat out get the best dollar benefit from your Medicare and supplemental insurance premiums when you can deduct them as business deductions. You can make this happen when:

• You are the sole owner and only employee of your C corporation.
• You operate as a sole proprietorship or single-member LLC, and your spouse is your only employee.
• You operate as a C corporation and have 20 or fewer employees to whom you offer group health insurance.
• You operate as a C corporation, either you or your spouse is an employee, and you offer a qualified small employer health reimbursement arrangement (QSEHRA).

Second Best: Self-Employed Health Insurance DeductionIf you are self-employed as a sole proprietor, an LLC member treated as a sole proprietor for tax purposes, a partner, an LLC member treated as a partner for tax purposes, or an S corporation shareholder-employee, you can potentially claim an above-the-line deduction for your health insurance premiums—including Medicare premiums.You don’t need to itemize deductions to get the tax-saving benefit from this above-the-line self-employed health insurance deduction. According to IRS Publication 535 (Business Expenses), the health insurance coverage must be established or considered to be established for your business as per the following explanations.If You Are a Sole ProprietorIf you are a sole proprietor or an LLC member treated as a sole proprietor for tax purposes who files Schedule C, a health insurance policy can be in the name of your business or in your own name. Premiums you pay for Medicare health insurance in your name can be used to figure the above-the-line deduction for self-employed health insurance.If You Are a PartnerIf you are a partner or an LLC member treated as a partner for tax purposes, a health insurance policy can be either in the name of the partnership (LLC) or in your own name. You can pay the premiums yourself, or the partnership (LLC) can pay them and report the premium amounts on your Schedule K-1 as guaranteed payments that you must include as income on your Form 1040.But if the policy is in your name and you pay the premiums yourself, the IRS says the partnership (LLC) must reimburse you and report the premium amounts on your Schedule K-1 as guaranteed payments that you must include as income on your Form 1040. Otherwise, the IRS says the insurance won’t be considered established for your business and you will not qualify for the deduction. The tax code allows the partnership (LLC) to deduct its guaranteed payments.If You Are an S Corporation Shareholder-EmployeeIf you are a shareholder-employee who owns more than 2 percent of the S corporation, a health insurance policy can be either in the name of the S corporation or in your own name. You can pay the premiums yourself, or the S corporation can pay them and report the premium amounts on your Form W-2 as additional taxable wages.But if the policy is in your name and you pay the premiums yourself as you would for your Medicare coverage, the IRS says the S corporation must reimburse you and report the premium amounts on your Form W-2 as additional taxable wages. Otherwise, the IRS says the insurance won’t be considered established for your business.What about a Spouse’s Medicare?In guidance, the IRS makes it clear that the S corporation and the partnership can reimburse to the shareholder-employee the spouse’s Medicare payments, and that reimbursement establishes the insurance in the business’s name. The S corporation then adds the reimbursement to the shareholder’s W-2, and the partnership treats the reimbursement to the partner as a guaranteed payment.The treatment described above creates the tax deduction for the spouse’s cost of Medicare (including supplemental insurance). If you operate as a proprietorship, we recommend having the proprietorship reimburse the nonowner spouse to establish the Medicare insurance in the name of the business.Employee Recreation and Parties Survive TCJA Tax ReformWhen you know the rules, you can party with your employees and deduct 100 percent of the cost. Interestingly, if you feed your employees during a training program, your deduction is only 50 percent. Make sure you know the rules that give you the 100 percent deduction for employee entertainment.The IRS says that the following types of entertainment qualify for the 100 percent employee entertainment tax deduction:

• Holiday parties, annual picnics, and summer outings
• Maintaining a swimming pool, baseball diamond, bowling alley, or golf course

The IRS makes it clear that the above are examples and that other types of entertainment may also qualify for the 100 percent entertainment deduction. The tax code states that “expenses for recreational, social, or similar activities (including facilities therefor) primarily for the benefit of employees” qualify for the 100 percent deduction.Who Are These Employees?Technically, the law requires that the entertainment expenses be primarily for the benefit of employees other than a “tainted group.” The tainted group consists of

• a highly compensated employee (an employee who is paid more than $125,000 in 2019);
• anyone, including you, who owns at least a 10 percent interest in your business (this is called a “10 percent owner”); or
• any member of the family of a 10 percent owner, i.e., brothers and sisters (including half brothers and half sisters); spouses; ancestors (parents, grandparents, etc.); and lineal descendants (children, grandchildren, etc., including adoptees).

As the business owner, you belong to the tainted group. That’s not a big deal. You just need to make sure that partying with the employees is primarily for the benefit of the employees.“Primary” Means “More Than 50 Percent”In tax law, the words “primary” and “primarily” mean “more than 50 percent.” For employee recreation, that means the untainted group of employees has to have more than 50 percent use of the entertainment facility, or in the case of a party, a majority of the attendees come from the untainted employee group.Documentation Tip. You can measure “primary” by days of use, time of use, number of employees, or any other reasonable method. Regardless of how you measure use, the keys to your deductions are the records that prove the uses.