If you chose to take COBRA health insurance after leaving a previous job, you may be able to deduct any premiums paid out-of-pocket. However, you are not. Enter the total annual premium paid by both the taxpayer and the Marketplace (not just the taxpayer's share of the premium) on the Family health coverage field. You can enroll through Connect for Health Colorado if you're a freelancer, consultant, independent contractor, or other self-employed worker. The best way to. Are health insurance premiums tax deductible? Yes, they are deductible if you have qualifying insurance and if you're an eligible self-employed individual. A health plan through Covered California is a great option for people who work for themselves. Freelancers, independent contractors and other people who don't.
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