I took a buyout from my regular job in December, received my buyout check in January, and received 6 months of paid COBRA from my employer. In July, I picked up the COBRA premium payments in full. I am also the sole proprietor of a freelance photography business, which has turned a profit for many years. That's now become my full-time job. Can I deduct the health insurance payments I made out of pocket for my wife and I on our 2017 tax return?
Sorry, but no. In order to deduct insurance premiums as a Self Employed Health Insurance Deduction, the policy must be "established, or considered to be established...under your business." Since you are continuing to purchase your insurance via the COBRA act through your employer, that would be considered established under that employer's business.
See IRS Publication 535 for more explanation of deductible business expenses. I've linked the publication below.
https://www.irs.gov/publications/p535#en_US_2016_publink1000208843
Sorry, but no. In order to deduct insurance premiums as a Self Employed Health Insurance Deduction, the policy must be "established, or considered to be established...under your business." Since you are continuing to purchase your insurance via the COBRA act through your employer, that would be considered established under that employer's business.
See IRS Publication 535 for more explanation of deductible business expenses. I've linked the publication below.
https://www.irs.gov/publications/p535#en_US_2016_publink1000208843
This is DEFINITELY a "gray area", but in my opinion (through several lines of reasoning), it is often probably deductible.
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