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Can I deduct health insurance premiums as a sole proprietor after taking a buyout from my job?

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?

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1 Best answer

Accepted Solutions
Kat
Level 15
Level 15

Can I deduct health insurance premiums as a sole proprietor after taking a buyout from my job?

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

*** I am NOT a tax expert. I am a seasoned TurboTax user, and volunteer to provide assistance to TT users. Nothing I post is to be considered TAX ADVICE; I bear no legal liability for responses.***

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3 Replies
Kat
Level 15
Level 15

Can I deduct health insurance premiums as a sole proprietor after taking a buyout from my job?

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

*** I am NOT a tax expert. I am a seasoned TurboTax user, and volunteer to provide assistance to TT users. Nothing I post is to be considered TAX ADVICE; I bear no legal liability for responses.***

Can I deduct health insurance premiums as a sole proprietor after taking a buyout from my job?

This is DEFINITELY a "gray area", but in my opinion (through several lines of reasoning), it is often probably deductible.
<a rel="nofollow" target="_blank" href="https://www.jklasser.com/askjk/my-wife-was-laid-off-from-a-job-and-took-cobra-now-shes-become-an-ind...>
Kat
Level 15
Level 15

Can I deduct health insurance premiums as a sole proprietor after taking a buyout from my job?

Thank you, @TaxGuyBill.
*** I am NOT a tax expert. I am a seasoned TurboTax user, and volunteer to provide assistance to TT users. Nothing I post is to be considered TAX ADVICE; I bear no legal liability for responses.***
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