I was told you’d just file a corrected W2 the next year.

on your W2 for 2018, I assume the income received would reflect the repayment (that is the important part) and the taxes withheld would still show the same as they were already paid. Then when you file, the tax software would automatically show your refund for the huge overpayment.

The problem is that the company still spent the money even if the IRS receives it instead of your bank account. As the departing pilot is leaving mid-contract, he or she is fully responsible to fulfill the terms and make the company whole.

Talk to a CPA. A tax attorney is overkill. If you received the payment in one year and repay it in the next, the rules changed with the new tax law. You need to talk with someone who knows what to do. More than likely, as I have seen with the tax law, you are screwed.

While I agree you should talk to a CPA, you should receive a corrected w2. As long as you have as much earnings as you have to pay back and don’t have a negative number it should be fairly straight forward. The big issue is SSI as there is no normal mechanism that you would file for a refund. The company has to refund that to you (or in this case get it back from the govt for you). I have had that done and when I entered info into TurboTax based on an estimate, it flagged the SSI amount and said to contact the employer for correction.

Many employers make you sign an agreement to pay back the gross amount, I don't know about Envoy. If you signed this then technically they can ask you to pay back gross even though it results in a tax loss to you. Assuming you didn't sign that:

See the links below for the correct way to handle this:
https://www.dickinsonlaw.com/blogs-a...f-compensation

Another source from Thomson Reuters Tax:
https://tax.thomsonreuters.com/blog/...nd-repayments/

Publication 15 with the IRS (wage repayments):
https://www.irs.gov/publications/p15...link1000202537

Unfortunately, most employers are too lazy/incompetent to correctly address this situation, and scare the employee into paying back the gross amount of the bonus, instead of the net amount, thereby screwing them out of social security and medicare taxes as a minimum.

If they do it correctly, the impact on the employee should net to zero.

Has anyone had any recent experience with this that could be shared?

Bonuses are taxed at 25 percent plus stare rate.

I'm going out on limb here, stare is state?

Yeah, auto correct and driving don't mix.