Can I write off the cost of private health insurance on my tax return?

Terry Says:  There is no simple answer to this question.   The first rule that might apply is the rule regarding all healthcare expenses, which can be deductible if they exceed, in total, 10 percent of your adjusted gross income.  However, there are also potential deductions of healthcare premiums for self employed people.  Under certain circumstances (including the fact that they do not qualify for employer-paid insurance) there is a deduction on page 1 of the 1040 tax form.  The deduction can be taken for the months — if not a full year — when you qualified under this provision.  But you can’t have a larger deduction than your earned income from the business.  I’m going to suggest that you ask your tax preparer, because the answer can vary depending on the circumstances.