The right question isn't “will courts issue a direct order to maintain a warrant canary to conceal a warrant (or, more likely, an administrative subpoena like an NSL) protected by a non-disclosure order”, it is “will courts punish signalling the existence of a warrant (etc.) protected by a non-disclosure order by dropping a warrant canary as they would any other action done to signal the existence of such a warrant.”
Which is why even the EFF doesn't recommend dropping the canary immediately but instead going to court to seek vindication of the right to drop the canary before so doing.
Which is why even the EFF doesn't recommend dropping the canary immediately but instead going to court to seek vindication of the right to drop the canary before so doing.