Yeah, any sort of trading instructions, even a binding instruction like "Sell my shares a year from today, when I won't be under lock up", is considered suspect

Yeah, any sort of trading instructions, even a binding instruction like "Sell my shares a year from today, when I won't be under lock up", is considered suspect for insider trading. A 10b-5 plan or similar is the only legally safe way to act during a quiet period. But trading during a post-IPO employee lockup, when there is no insider information concern, maybe isn't as tight as "the week before earnings release". Seems like it shouldn't be legally. But employers certainly would order their employees not to trade. There was a nasty loophole/scandal a few years back where people would set up a legal auto-sale plan like "Sell 1000 shares every week", and selectively cancel the plan on weeks they didn't want to transact. I'm not sure what became of that.