Unemployed for 9 months and did not receive any unemployment assistance. I used stock sales to finance my family and paid for my own insurance. How do I file this?

I was unemployed for 9 months and did not receive any unemployment assistance. I used stock sales to finance my family and paid for my own family health insurance. Is there an advantageous way to file this to obtain a lower tax rate on my personal retirement stock sales?

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Expert Alumni

Jun 4, 2019 10:08:31 PM

Unfortunately no. Any gain from the sale of stock is taxable income. There are no exceptions for a person in your circumstances. You may, however, take a deduction for your health insurance expenses as part of you medical deductions on Schedule A if you itemize your deductions. Deductible medical expenses are those that exceed 7.5% of your adjusted gross income in 2018.

[Edited 03.25.2019 | 3:39 pm pst]

New Member

Jun 4, 2019 10:08:32 PM

But do I get credit for paying family health insurance out of pocket?

Expert Alumni

Jun 4, 2019 10:08:33 PM

Yes, please see my edited answer.

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Unemployed for 9 months and did not receive any unemployment assistance. I used stock sales to finance my family and paid for my own insurance. How do I file this?