I am retired/not receiving income from my past employer. I am able, to purchase unsubsidized medical insurance from my past employer. Is it tax deductable?

[DavidD66]

The Cobra premiums you pay your former employer are potentially tax deductible, but only if you itemize.  Additionally, the amount you can deduct for medical expenses is limited to the amount in excess of 7.5% of your adjusted gross income (AGI).  So, if your AGI is $100,000 and your medical expenses are $10,000 you can include $2,500 as an Itemized Deduction.  If you are self-employed, you cannot take a deduction for self-employed health insurance for COBRA payments since it is an employer sponsored plan.    

[bmoyer]

Is this true? He is no longer employed. So depending on how you interpret the wording of "employer", shouldn't he be considered not an employee, therefore it is not an "employer sponsored plan"?

[DawnC]

The COBRA policy is considered an employer-sponsored plan.   COBRA premiums would not qualify for the Self-Employed Health Insurance (SEHI) deduction but they do qualify as a personal medical expense on Schedule A if you itemize.   @bmoyer 

Any SEHI deduction-qualifying policy has to be in the taxpayer's name or their business's name.   See this article on Form 7206.

[bmoyer]

Interesting.. I have a related question: As a sole-proprietor, retired from general employment, if a former employer offers a Medicare advantage plan, dental insurance, and vision, and the costs are deducted from my pension check from that former employer,  are the costs of those plans (i.e. the amount deducted) include-able in SEHI?

[DawnC]

Yes, the premiums deducted from your pension count.   @bmoyer    Qualifications for the deductions are as follows:

• You must have a net profit from your self-employment (reported on Schedule C). Your deduction cannot exceed the net earned income from that specific business.   AND
• You cannot take the deduction for any month in which you were eligible to participate in a health plan subsidized by an employer (including a spouse’s employer).