For anyone curious: the current legal take is that something that you intentionally remove, do not update, or otherwise change your regular course of action for that either directly alerts, or is understood to mean to alert, users to warrants and surveillence attempts, would violate the secrecy part of the order, as you are doing something (or not doing something that you would normally do) that would be understood with little ambiguity to mean to be disclosing the attempt.
The current opposing take is... first ammendment, and free speech takes precedent here. Maybe a touch of 5A too, TL;DR the government cannot force someone to lie.
I don't know how many cases of these have made it to court. But I do damn well know that the courts know of canaries, and if push comes to shove, the courts have no issue claiming that the bill of rights doesn't apply, whenever it's inconvenient.