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I wish I had known about an 83b. Sadly I didn't. Regarding another issue with this sale, my taxes are problematic. At this point, I plan to employ a CPA rather than do my own taxes. The W-2 is because the ISO triggered as disqualified despite me holding the stocks for the full qualifying timeline. Pursuing the company to correct the W-2 has proven fruitless. 

 

The sale triggered in 2021 and I was issued a payment. 

Then I received an email and a second, much smaller payment in 2021. 

The sale is now being brokered/handled by Fortis, who has listed 2 more pending payments (one for 2022 and one for 2023). Both held in escrow pending certain things like legal fees. 

 

I mainly am pursuing a CPA at this point because i'm not sure how to handle my cost basis for 4 separate payments, 2 of which aren't even in this tax year. 

 

If it were 1 payment, I know for a disqualified ISO sale, my cost basis becomes my W-2 box 1 amount (the W-2 only has the stock sale, nothing else). But I am not sure for the other payments. Or maybe box 1 is my total cost basis for 2021?