If I trade PTO to pay for LTD, can I write that off as a deduction?

[ToddL · Accepted solution]

No, you cannot claim a deduction for trading unused Paid Time Off (PTO) for Long-Term Disability (LTD) insurance coverage.

Unused PTO has never been "paid out and taxed" to you - unless you paid taxes on the value of the PTO, you cannot claim a deduction when using it for something else.

If you were taxed on the PTO when you traded it for LTD coverage, you still wouldn't get a tax deduction for the cost of the LTD. Disability insurance is not deductible on your tax return. You would not, however, have to pay tax on any disability payments from policy you paid for with after-tax funds.