Mogadishu is correct. COBRA health insurance premiums paid out-of-pocket are not eligible for the self-employed insurance deduction as the plan is still under your former employer’s name. However, you can claim the premiums as medical expenses on Schedule A if they exceed 7.5 percent of your AGI. This deduction is only available if you itemize your deductions and only if your total itemized deductions are higher than the standard deduction.
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