A modeled ISO sale can be a disqualifying disposition when its timing does not satisfy the special ISO holding requirements.
Check the dates first
Review the grant date, exercise/acquisition date, and sale date for the specific shares. The general ISO holding requirements include holding beyond two years after grant and one year after transfer on exercise; confirm the exact dates and applicable exceptions with the client's tax professional. IRS Publication 525.
Review the plan
Open the client → Plans → Build.
Open the saved plan and expand the sale action.
Verify the grant/lot, quantity, exercise date, sale date, and tax treatment.
Check whether a strategy or an imported plan supplied the action timing.
Duplicate the plan before testing another sale date.
Changing the proposed date can change cash availability, market exposure, and taxes together. Do not alter an actual historical date to force qualifying treatment.
Compare the full result
Use Tax to review compensation income, capital gains, AMT, and the relevant years. Use Cashflow to check whether the alternative timing meets the client's cash needs.
If the classification still looks wrong, reconcile the lot connections and recorded exercise history. See Record completed transactions and ISO planning.