Capital losses on underwater stock and options
When the price falls below your exercise value, the tax code offers partial relief — but slowly.
Exercised shares
Selling below your cost basis produces a capital loss that offsets capital gains without limit and up to $3,000 of ordinary income per year, with the remainder carried forward.
Same-year ISO rescue
If ISO shares crater in the same calendar year you exercised, selling before December 31 removes the AMT preference item entirely and converts the event to ordinary income on the realised amount.
Worthless options
Options that expire unexercised produce no deduction because you never had basis. The loss is economic, not tax-deductible.
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