Medical insurance premiums paid out of pocket while out of work

[moneymker1]

Medical insurance premiums paid while on disability from work

[DoninGA]

Health insurance premiums you paid with out of pocket funds and were not reimbursed can be entered on Schedule A as an itemized medical deduction.

Health care insurance premiums and other medical expenses that you paid with out of pocket funds are an eligible medical expense that you can deduct using Schedule A for itemized deductions. However, only your total medical expenses that are greater than 7.5% of your Adjusted Gross Income (AGI) can be deducted. Your total itemized deductions reported on Form 1040 Schedule A must be greater than the standard deduction for your filing status to have any tax benefit.

Standard deductions for 2021

• Single - $12,550 add $1,700 if age 65 or older
• Married Filing Separately - $12,550 add $1,350 if age 65 or older
• Married Filing Jointly - $25,100 add $1,350 for each spouse age 65 or older
• Head of Household - $18,800 add $1,700 if age 65 or older

[VolvoGirl]

Yes you can deduct it  if you have enough total deductions to itemize. 

Federal On left

Deductions and Credits at top
Scroll down to Medical – Medical Expenses

You can only deduct the amount of unreimbursed Medical Expenses you actually paid over 7.5% of your AGI. And then all your itemized deductions have to be more than the standard deduction to get any benefit (so you would only be getting the benefit of the amount that puts you over the standard deduction). And since the Standard Deduction is increased more people will not need to Itemize.

For 2021 the standard deduction amounts are:

Single 12,550 + 1,700 for 65 and over or blind (14,250)

HOH 18,800 + 1,700 for 65 and over or blind (20,500)

Joint 25,100 + 1,350 for each 65 and over or blind (26,450/27,800)

Married filing Separate 12,550 + 1,350 for 65 and over or blind (13,900)

Or if you are filing as Married Filing Separately and your spouse itemizes then you have to also itemize even if it is less than the Standard Deduction even if it is zero.