They have included a warrant canary
They have included a warrant canary
[0]: http://jolt.law.harvard.edu/articles/pdf/v28/28HarvJLTech525...
There has been no test cases on the subject, and there are few instances of the court upholding compelled speech. Further, the precedents that we do have for compelled speech have been based on the compelled speach being truthful (as well as a legitimate government interest in compelling the speach).
This means that, irrespective of the law of the gag orders, one could make a very strong consitutional arguement for being allowed to remove the canary, and would have strong precedent.
Every service then has to kill its canary.
If you truly believe your argument, you wouldn't prosecute the boss even in the presence of this email. We all know anyone planning on using a warrant canary is intending to inform the public, so whether or not there's an email admitting it should be irrelevant if the action is legal. If you believe that the boss is not guilty, then you're consistent in your position.
Now, as a practical matter, you'd use an in-person meeting or telephone call or something. Or you'd at least use different wording. But the act itself would in principle still be illegal, even though there is no evidence to prosecute. And in that sense, a warrant canary could be a useful tool to allow one to get away with a crime that they consider unjust.
However, I found this Quora answer to give pretty good justification on national security grounds for military scenarios:
https://www.quora.com/Why-is-the-government-afraid-of-reveal...
When you receive an NSL, you either publish a document including the phrase "Today is 2016-09-03." or else simply stop publishing that document and leave the one with the old date up, and let people draw their own conclusions.
Under this scheme, the court would have to compel speech on your part (force you to publish a new canary), but there's some precedent that might indicate that you can tell them to stuff it.
https://github.com/WhisperSystems/whispersystems.org/issues/...
Bruce Schneier: Personally, I have never believed this trick would work. It relies on the fact that a prohibition against speaking doesn't prevent someone from not speaking. But courts generally aren't impressed by this sort of thing, and I can easily imagine a secret warrant that includes a prohibition against triggering the warrant canary. And for all I know, there are right now secret legal proceedings on this very issue.
https://www.schneier.com/blog/archives/2015/03/australia_out...
At the very least, the issue isn't clear-cut, and there most certainly isn't constitutional precedent.