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I've just started my new job as a 1099 employee having worked as a full time employee for 4 months. For health insurance I'd like to do Cobra since my family has already met their deductibles for the year. Im trying to figure out if my Cobra insurance is tax deductible. From what I've read since the insurance is not established in my name I normally can't deduct it. However it seems like since I worked as fulltime employee for the first 4 months of the year I should be able to deduct cobra expenses from that income.

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For the first four months of the year, when you were an employee, the health insurance premiums were paid for with pre-tax money. When you receive your W-2 at the end of the year, the amount in Box 1 of the W-2 will be reduced by the amount you paid for health insurance. You can't deduct it on your tax return because it has already been deducted for you.

Now that you are a 1099 independent contractor, you are self-employed and eligible for the self-employed health insurance deduction. However, as you noted, the COBRA premiums are likely not eligible for this deduction, because the policy is in your old employer's name. See this question for details, but keep in mind that there are conflicting answers on that question.

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While COBRA premiums are not eligible to be a "business" expense they can be a medical expense for personal deduction purposes. If you're itemizing your deductions you may be able to deduct that way. However, you will only be able to deduct the portion of the premium that exceeds 10% of your AGI.

Are you a full time employee now or are you a 1099 contractor? Do you have access to your employers health plan?

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