Hi @GeorgeM777 ,
Let me clarify the first question. The ISO same-day sale was not at a loss - all ordinary income, no ST gain or loss. Four days later, an RSU release/sell-to-cover had a $1000 loss. Since none of the ISO same-day sale shares were owned at the time of the RSU sell-to-cover loss, was the RSU loss a wash sale?
To clarify the second question - assume the RSU release/sell-to-cover with a $1000 loss happened first. Then four days later, an ISO same-day sale (again all ordinary income, no ST gain or loss) happens. In this case, does the RSU sell-to-cover get reported as a wash sale, then the ISO same-day sale needs an adjustment of $-1000 since it's within the 30-day window?
These events happened in different brokerage accounts, so the brokers don't report any wash sales, but I am sure the IRS knows:)
