USA Wash sales with ISOs & RSUs vesting in parallel

Mar 22, 2020
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United States
Hi All, I joined a pre-IPO company few years back and got ISOs, vesting every month. The company went IPO last year, and I received an RSU grant after it went IPO. So, right now (and for next 1 year), I will have monthly ISOs vesting and quarterly RSUs vesting.
  1. Do the monthly vesting ISOs count towards wash sale? Say, I sold my RSUs on Mar 23th, and had ISOs vest on Apr 1, would this be a wash sale? Or, do ISOs count towards wash sale only when they are exercised?
  2. Need advise on my current situation. I exercised my ISOs early this year (2020), and the stock market tanked (Coronavirus) shortly after. I also got an RSU grant last year, and they started vesting quarterly starting Sep-2019. I did a quick calculation regarding AMT on ISO exercise, and found that if I sold the exercised ISOs in 2020 itself, my short term capital gains tax will be $1.5K less than AMT. The exercised stocks are still in profit. The RSUs I vested over last 6 months (Sep-2019 till Mar-2020) have a high cost basis - the current market stock prices is much lower than the cost basis. I'm thinking of selling all the vested RSUs and some exercised ISOs so as to cover my ISO profit with RSU loss. What is your advise? What should I do? My next RSU vest is in June, and the ISOs will keep vesting beginning of every month.

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