1. 15645 POINTS
    Edward HarrisPRO
    Owner, Best Health And Car Insurance Rates - Instant Online Quotes, US
    Deducting your healthcare premiums is not only possible, but makes financial sense. I'll use myself as an example.

    I have been an insurance broker for 33 years so there may not be a better resource. I own an HSA (along with the High-Deductible-Health-Plan) and have been a supporter of this type of policy for many years.

    Although I may file my taxes differently than yourself, I am able to deduct a portion of the premiums along with the proceeds that are deposited into the HSA.

    A self-employed person can deduct health insurance on their taxes in a number of ways. However, whether you use Turbo-Tax or simply complete your own tax return without help, it s always wise to consult a tax expert or the IRS website regarding deductibility of health insurance.

    And remember that premiums and actual expenses may be treated differently as well persons that itemize vs. not itemizing.
    Answered on May 25, 2013
  2. 1380 POINTS
    James Elbaum
    President | Founder, CLM Insurance Group, Delray Beach, FL
    The best way to get deductions on your taxes using health insurance is to purchase a HIGH Deductible Health Plan (HDHP) and open a health savings account (HSA) with it.  The money you put in the HSA over the coarse of the year is tax deductible with the following limits:


    $3300 - Individual 2014
    $3300 + $1000 - Individual 2014 (55+ Contribution)
    $6550 - Family 2014
    $6550+ $1000 - Family 2014 (55+ Contribution)

    To learn more about HSA coverage visit CLM Insurance Group
    Answered on April 19, 2014
  3. 2775 POINTS
    Joe 'Gravy' Graves
    Owner, I Hate Buying Insurance, Nashville TN
    WOW... a lot has changed regarding that subject just since 12/2015. The IRS is a total mess when it comes to this subject. The answer is YES... & NO... SO MUCH depends on your company structure (Sole Prop, LLC, C or S Corp)... Your role and how you are paid is vital to know.

    The Tax Code.... sucks... It should be allowed...easily. Yet it is not. Silly that if you had a "group plan" for you and ONE employee, then YES, the destructibility is there. Yet as a one person shop (assumption being made here), it's NOT easy. Reach out if you have any more questions. -gravy.
    Answered on March 24, 2016
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