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If you qualify, you get the health insurance deduction whether you purchase your health insurance policy as an individual or have your business obtain it. If you purchase your health insurance plan in the name of one of your businesses, that business will be the sponsor. However, the IRS says you may purchase your health coverage in your own name and still get the self-employed health insurance deduction. (IRS Chief Counsel Memo 200524001.) This tactic might be advantageous because it allows you to pick which of your businesses will be the sponsor at the start of each year. Obviously, you should pick the business you think will earn the most money that year.
Moreover, if you have more than one business, you can have one purchase medical insurance and the other purchase dental insurance and deduct 100% of the premiums for each policy, subject to the income limits discussed above. This approach will be helpful if no single business earns enough income for you to deduct both policies through one business.
Because the self-employed health insurance deduction is a personal deduction, it doesn't go on your Schedule C if you're a sole proprietor. You deduct it in the "Adjustments to Income" section on Schedule 1 of Form 1040. If you itemize your deductions and don't claim 100% of your self-employed health insurance costs on Schedule 1, you may include the rest with all other medical expenses on Schedule A, subject to the 7.5% of Adjusted Gross Income limit. You would have to do this, for example, if your health insurance premiums exceed your business income.
To learn more about what you can deduct, see Nolo's Personal Tax Deductions and Tax Breaks section.