Would it be of benefit to you if you, say, had some other deductions that alone wouldn't get you over the standard deduction, but if you took your health insurance premiums taxed, that would put you over the standard deduction for the year, thereby saving you on the tax bill.
A very simplified look at one's income is below. Whether the insurance payments are subtracted immediately from gross salary, or later as part of itemized deductions, the result is the same. And that's assuming there are enough other medical expenses to allow full subtraction of the insurance.
In addition to the SS wage base item noted above, there is another item in the tax code that could be affected: the Earned Income Credit. Part of the EIC calculation uses the "salary reported on a W-2" and in some ranges the EIC increases as that salary increases.
Similar to what the SS folks do, it's possible an employer's pension calculation uses the SS wage base instead of gross income.
Also, you could decline coverage from the employer's health plan and buy it yourself using after-tax dollars.
In short, there could be reasons, in specific employer or employee situations, that make it better to eschew the pre-tax route - but for most people pre-tax will be better.
Gross salary
-
Pre-tax med. ins.= Soc. Sec. wage base
Soc. Sec. wage base
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401k contribution= Salary reported on a W-2
Salary reported on a W-2
- Traditional IRA
-
Student loan interest= AGI
AGI
- Deductions
-
Exemptions= Taxable income