I have an initial vest date on a Sunday. An eight-week insider trading blackout begins the following Monday. Should I expect my shares to be sellable in my E*Trade account on the preceding Friday? Or am I gonna have to hold them for two months? I’m not concerned about my company, but about the broader market taking a downturn during the blackout period.
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Yup, you're going to have to hold. One way to avoid this situation is to setup a 10b5-1 trading plan prior to the blackout period.