Can A Sole Proprietor Deduct Health Insurance Premiums? 
Yes providing that the sole proprietor is not eligible to participate in a group health insurance plan . Eligibility is determined on a month to month basis . What this means is , if you are a sole proprietor with a spouse who is employed and has access to group health insurance , you are NOT able to deduct health insurance premiums paid on a plan purchased in lieu of the employers group coverage . This holds true for all months that your spouse is employed and is eligible to participate in the plan . Another example of ineligibility would be a sole proprietor who also has a part or full time job where group health insurance benefits are available from that job . 