Were all the dividend reinvestment shares sold on the same date? If so, you can enter as a single entry for all the long-term and another single entry for all the short term transactions. If all the shares from dividend reinvestment were sold on the same date, and they were all long-term, you would have a single transaction. You would enter the combined proceeds and cost basis. You would use Various as the date acquired. If you have multiple sales, for each sale date, you will have either one or two transaction. I would enter them separate from the ESPP info if you are using the program's guided entry.
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