Tax
Qualifying Disposition
A sale of ISO or ESPP shares that meets the holding-period tests — held more than 1 year after purchase/exercise AND 2 years after grant — unlocking the favorable tax treatment.
For ISOs, a qualifying disposition converts the entire spread from exercise price to sale price into long-term capital gain — no ordinary income at all. For ESPPs, it caps the ordinary-income piece at the plan discount (measured at the offering date) and treats the rest as long-term capital gain.
Miss either holding period and the sale is a 'disqualifying disposition': the bargain element becomes ordinary income, taxed at regular rates. For ISOs, disqualifying in the same year as exercise at least unwinds the AMT problem — occasionally a deliberate strategy when the stock has fallen.
Both clocks matter and they run from different dates: one from grant (or the ESPP offering date), one from exercise (or the ESPP purchase date). A sale can satisfy one and still fail the other.
Common pitfalls
- Selling ISO shares even one day before the holding periods are met — the entire favorable treatment is lost, not prorated
- Holding ISO shares purely to qualify while the stock tanks — the AMT paid at exercise was real cash against a gain that evaporated
- Trusting the broker's 1099-B basis on ESPP qualifying dispositions — it usually omits the ordinary-income component and causes double taxation unless adjusted
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