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Hi @DavidD66 - Just finally getting back to my taxes after a Covid hiatus. As I went to enter the 1099-B (with recognition that the 1099-B is probably wrong) and it makes sense what you said - the amount reported in Box V is much larger, so if I "include that bargain element" - how would I calculate the new Cost Basis? Would it be the same amount as what is reported as Income in Box V, or the Total Proceeds from the Sale...? (Box V is about $18K higher than what's in the Proceeds...wow, I'm confused)

 

Also, on the second part - since this was a single cashless transaction - there is no difference between the value at the time of the stock at the time of exercise (your cost basis) and the value at the time of sale (proceeds), because that was all one transaction. Am I interpreting that correctly?

 

Thank you in advance for clarification!