They have never allowed "Various" for sales date.  But most of the transactions now don't need it, because they are Box A or D.  Those with basis not reported, are supposed to be listed separately.  These rules are made by IRS employees who go to H&R Block for tax return preparation.  The worst cases are when withdrawals are being made monthly from a mutual-fund account. The purchase date might go back to the 1980s.  Just because the software doesn't allow for common sense, doesn't mean you are forbidden to use it.