This article is wrong in some significant ways. If you buy out incentive stock options (ISO’s) within 90 days of leaving, then that’s not a taxable event. You w

This article is wrong in some significant ways. If you buy out incentive stock options (ISO’s) within 90 days of leaving, then that’s not a taxable event. You will not end up paying regular income tax on the paper profit. That’s a large point of the benefit of receiving ISO’s. Now - you may very well have to pay Alternative Minimum Tax (AMT), as AMT rolls in some otherwise non-taxable transactions into the calculations, this being one of them. The real kicker is - let’s say you do pay AMT on the paper gains, and then the stock tanks later - you can’t claim that as a loss on your taxes. You can take a credit for the excess that you paid in AMT, but you can only take that a few thousand dollars at a time. So, OP could be in a situation where the shares eventually sell $0.01 in the money, so they would re-earn their $100k investment, but effectively lose the $200k AMT bill (if that’s accurate). Additionally - you actually can not negotiate to extend the expiration of your purchase option after you leave, because it’s codified in IRS regulations. Companies CAN choose to let you have longer, but then the options become non-qualified stock options, and lose some of the benefits of ISO’s, primarily the non-taxability of the exercise event.