Again: if you are told not to communicate something, you don't communicate it. How come the CEOs who try all sorts of crazy things to work around insider trading haven't tried this?

Given that Reddit has exercised their warrant canary already and other big companies have them, apparently actual lawyers think it's a valid strategy.

You have no idea what is going on with Reddit or Apple. I know the EFF is eager to get people to sacrifice themselves on this altar. That says more about the EFF than about the state of law.

I think being put under a security order you can't discuss is a serious liberty problem. It doesn't follow that some crazy scheme is the right reply.