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You will have to enter them in multiple transactions, according to the discount rate.
More specifically, you need to report your one sale as two different sales, one for the 15% discount period and another for the 5% discount period. Naturally the "proceeds" for each sale is allocated by the number of shares sold in each sale and totals the amount of proceeds reported on the 1099-B.
Breaking the one sale into two sales will then allow you to report the discount correctly for each group of stocks.
Tom Young
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