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Get your taxes done using TurboTax
Thank you for that additional information. In terms of amending a prior return, if the ISO was re-purchased in 2021, then there is no need to amend your 2019 return. Report the ISO re-purchase as you would any other ISO in which you exercised the ISO and then later sold the shares. You are correct in that because your cost basis and the re-purchase price are the same, you will not have a gain or loss.
The same would apply for the NQSO exercise and re-purchase. Although here, it looks like you will have a capital loss.
To the extent you paid tax on the early exercise, you won't be able to get any of that money back. That's one of the downsides to early exercise in that there are no refunds for prior tax payments.
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‎April 11, 2022
3:53 PM