When you say "Since the ISO event was same day," if you mean that you exercised your option to purchase shares and then sold those shares at a loss, then yes, the ISO loss would have been a wash sale because of the RSU vesting. The IRS considers RSU vesting as the functional equivalent of a purchase. Thus, your ISO event was a purchase and a sale at a loss, and then your RSU event was a purchase followed by a sale at a loss. Thus, the ISO loss would be characterized as a wash sale and the loss would be disallowed.
Regarding your second question, if the ISO purchase and sale occurred four days after the RSU vesting, and the ISO sale resulted in a loss, then the RSU vesting would also trigger the wash sale rule. In this scenario, the ISO loss would be disallowed.
@bluecloud33
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