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You can do it either way. There is a slight chance that you may get a letter from the IRS if you combine the multiple sales, but it will be easily explained. Do whatever is easiest for you.


Thanks. I'm not sure I want to take a chance on getting a letter from the IRS, so I think I'll just take the time to itemize everything to match the 1099-B (although it's not going to match anyway by the time I break out the short-term and long-term shares).

Oh well, one follow-up question that came to mind as I was sorting through the various line items. Since the fractional shares were actually acquired during calendar year 2008, my initial thoughts were that the "Cash in Lieu" liquidation of those fractional shares would necessarily be a short-term gain/loss. However, when applying the FIFO methodology, that does not appear to be the case. Am I correct in presuming that using the FIFO methodology, I would need to reflect not only a cost basis based on the cost of the original lot of shares purchased (before the fractional shares were acquired) but also reflect the actual date those original shares were actually purchased in the "Date Acquired" field? Thus, that would make the sale of the fractional shares actually a long-term gain/loss?
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