ESPP Stock Sale Entry in FreeTaxUSA When entering ESPP sales with unknown acquisition dates: (1) Select "Yes" to ESPP question to trigger ESPP-specific flow; (2) Choose "No" for known acquisition date, then select "Various Dates Acquired - One Year or Less" (short-term conservative default); (3) Enter sale proceeds and date; (4) Set cost basis to $0 if no supplemental statement available and W-2 Box 14 shows $0 ESPP income; (5) Select "No" for basis reported unless Box 12 is checked on 1099-B. This preserves the full gain for reporting and avoids understating tax liability. ---