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If, while my wife was out on leave, she had to pay her medical insurance premiums via check (i.e. not through payroll deductions), and therefore, these out-of-pocket medical premiums paid were not reflected on her W-2 as a reduction to her taxable income, we were debating whether we could "manually adjust" her taxable income for these premiums paid since they were paid to an eligible tax-free cafateria plan? It makes sense to me that the tax treatment should be the same (i.e. tax free) regardless of whether they were paid via payroll or via a written check?

3 years, 2 months ago on Consider the Impact On Your Finances When Taking a Paid Leave of Absence, FMLA, or Disability From Work