Q: I sold ESPP stock all on one date, but I acquired all the shares over the last 6 years through a weekly payroll deduction. There is a different FMV, grant date, etc. for every single week. Do I have to report every single one of those on my return? That would be hundreds of lines.
A: The IRS wants to see the sale prices and dates to match up with their reports. Your calculation of basis is your own, and can be reported as just a total.
The dates acquired can be "VARIOUS" to avoid having to list out every purchase date. As long as they get the same tax treatment (e.g., long-term capital gains), this will be fine.
If you purchased some shares that were held less than a year before you sold, you should report them separately, also with "VARIOUS" purchase date, and classify them as short-term capital gains.
You might have just one transaction to report (if they are all long-term holdings), or maybe a second (for the short-term holdings).
-- Answer from Perry D., an accountant on JustAnswer.
Daily Answer is excerpted from the JustAnswer archives and features information provided by a Expert on JustAnswer.