Where to enter Post Tax Health Insurance Premiums when on Long-Term Disability and employer uses 3rd party to issue disability payments and health insurance is billed directly to employee

[wilsontax1]

As the Subject states, when I transitioned to Long-Term disability, my employer no longer issues my paychecks which had pretax deductions for my medical/dental/vision. Since being on LTD, a 3rd party handles my paychecks, and what was once a pretax deduction (medical/dental/vision) is now paid out of pocket by debiting my checking account. How do I account for the health insurance premiums that I paid with post tax dollars. In 2024 I have 3 months of post tax health care premiums that I want to deduct. I see references to deducting this under medical expenses, but subject to the 7.5% rule. This doesn't seem to be the right area to account for this, as I'm simply trying to adjust my taxable income, i.e. had my employer continued to take out my pretax medical costs from my paychecks while on disability. I got a W2 from my employer (box 1 nets out medical premiums) and a W2 from 3rd party (box 1 is gross distributions). Please help.

[BillM223]

Have you asked this 3rd party about the W-2 that they send you?

1. Is the health insurance premium included in the Box 1 amount?

2. If the health insurance premium is not included in box 1, then would it not be appropriate to include a code DD in box 12 with the amount of the health insurance premium?

4. Is this 3rd party the one debiting your checking account for the health insurance premium, or is it someone else?

I am curious to their thought process.