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The stock option deduction loophole is one of the most unfair and regressive tax loopholes of all. Stock options get treated like capital gains. That means it allows those with stock options to pay tax at half the rate everyone else pays on their employment income.
Unfortunately, not all stock options are transferable -- meaning you can not leave unexercised options to a loved one in your Estate Plan. In these cases, the stock options would expire at the time of your death. Even if your stock options are transferable, some companies limit who they can be transferred to.
You have taxable income or deductible loss when you sell the stock you bought by exercising the option. You generally treat this amount as a capital gain or loss. However, if you don't meet special holding period requirements, you'll have to treat income from the sale as ordinary income.
Stock options are typically taxed at two points in time: first when they are exercised (purchased) and again when they're sold. You can unlock certain tax advantages by learning the differences between ISOs and NSOs.
TLDR Exercise early and File an 83(b) Election. Exercise and Hold for Long Term Capital Gains. Exercise Just Enough Options Each Year to Avoid AMT. Exercise ISOs In January to Maximize Your Float Before Paying AMT. Get Refund Credit for AMT Previously Paid on ISOs. Reduce the AMT on the ISOs by Exercising NSOs.
Understanding Inherited Stock Options If you inherit stock upon the original owner's death, your first task will be to check the paperwork that comes with the options to determine whether they expired upon the original holder's death. Some options expire on the death of the holder, and others do not.
If you have an immediate need that can't be put off, selling your shares and using the gains could be a better alternative to taking out a loan or accruing debt. In some cases, you might want to act now if you expect costs to rise.
A transfer of employee stock options out of the employee's estate (i.e., to a family member or to a family trust) offers two main estate planning benefits: first, the employee is able to remove a potentially high growth asset from his or her estate; second, a lifetime transfer may also save estate taxes by removing ...