Unfortunately, COBRA policies do not meet the requirements for claiming the self-employed health insurance deduction. Specifically, as the COBRA policy would have been setup under the name of your prior employer, it does not meet the requirement of the policy being setup under your name or your business's name.
However, the premiums from your COBRA policy may be deductible as an itemized medical expense deduction on Schedule A to the extent that 1) your total out-of-pocket medical expenses are greater than 7.5% of your Adjusted Gross Income, and 2) your total itemized deductions are greater than your standard deduction.
See the following from IRS Publication 535:
The insurance plan must be established, or considered to be established as discussed in the following bullets, under your business.
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For self-employed individuals filing a Schedule C, C-EZ, or F, a policy can be either in the name of the business or in the name of the individual.
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For partners, a policy can be either in the name of the partnership or in the name of the partner. You can either pay the premiums yourself or the partnership can pay them and report the premium amounts on Schedule K-1 (Form 1065) as guaranteed payments to be included in your gross income. However, if the policy is in your name and you pay the premiums yourself, the partnership must reimburse you and report the premium amounts on Schedule K-1 (Form 1065) as guaranteed payments to be included in your gross income. Otherwise, the insurance plan won’t be considered to be established under your business.
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For more-than-2% shareholders, a policy can be either in the name of the S corporation or in the name of the shareholder. You can either pay the premiums yourself or the S corporation can pay them and report the premium amounts on Form W-2 as wages to be included in your gross income. However, if the policy is in your name and you pay the premiums yourself, the S corporation must reimburse you and report the premium amounts on Form W-2 in box 1 as wages to be included in your gross income. Otherwise, the insurance plan won’t be considered to be established under your business.
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