Ordering you to update the canary is in effect, ordering you to make affirmative, untrue statements about your products, namely that they are secure against government surveillance. Do I think they'd threaten you with obstruction? Yes. Do I think they'd threaten to send you to jail? Yes.
But do I think they'd arrest you and try you? I am not sure. They might. But once they do that, they are in a bind. They lose the leverage against you revealing the specifics of the warrant (other than that there was one somewhere), and they go past the point of no return, where you have to fight back and challenge the Constitutionality of the order to lie. I won't give advice (IANAL, etc) but I think the most likely outcome would be a game of chicken. It would be a public fight (you have a right to a free and public trial with all evidence submitted in open, public court, obviously including the NSL or warrant!), and they'd risk an adverse judgement handing a tool to everyone to resist this.
So if they are willing to try you and admit the NSL or warrant as evidence, they are then revealing more than you have, and this undercuts their case.
Maybe. Then again, these things (NSLs) are supposed to be about national security, aren't they? As of now I don't think the intelligence establishment is mad enough to disappear a "well standing" (white male?), resourceful citizen -- seeing as the entire idea of these secret laws are clearly illegal by any sane definition -- but how long will that last?
Also, remember that if this is part of some semi extra-legal investigation, one or more of the agencies involved might pressure you with black mail of some sort. Or a mix of black mail and prison.
But yeah, I think the reality of the situation is: comply, or government will frown on you and your business, and that might be the end of your business (at least you can forget about having new radio spectrum for your wireless, or any other licence you might need, etc...).
It would be easy to go through ever phone call and financial transaction until they find a true but incidental or trivial felony to hit you with.
Whether you subscribe to the Richelieu argument or not, I know 25-50% of first time home buyers are open to the head-shot. (borrowing money on the side from family or friends for their down payments - a federal felony)
Look at how they took down Joseph Nacchio for denying the 2001 (illegal) tapping requests.
In theory you have a right to a public trial, but it seems to me that the government has been ignoring more and more rights lately (of course, a lot of this is just better coverage than we had 30 years ago).
I don't know about more courage. Look at how many people in Washington State lost their jobs due to being accused of Communist involvement in the Canwell hearings in the 1940's. The mere accusation was enough to cause people to be fired and blacklisted, setbacks from which they would never recover fully.
I think less things change than everyone likes to think. We were just living in a more protected time after the McCarthy approach was deemed to be Un-American. The cycle is swinging back the other way, and it will be perhaps a few decades before it recovers (if it does).
The real danger from where I sit is actually that for things to recover we need a vibrant middle class. We need people like John Caughlan (my mother's uncle) who went to Harvard but then dedicated his life to fighting for the politically persecuted to an extent he was even kicked out of the ACLU for defending the unpopular (the ACLU later apologized and gave him their William O Douglas Award). You can't have that if everyone comes out of college with crushing student debt and you can't have that if small businesses and self-employment becomes prohibitively regulated. The economic and political realities are unfortunately intertwined in a way that makes me pessimistic sometimes.
Ordering you to update the canary is in effect, ordering you to make affirmative, untrue statements about your products, namely that they are secure against government surveillance. Do I think they'd threaten you with obstruction? Yes. Do I think they'd threaten to send you to jail? Yes.
But do I think they'd arrest you and try you? I am not sure. They might. But once they do that, they are in a bind. They lose the leverage against you revealing the specifics of the warrant (other than that there was one somewhere), and they go past the point of no return, where you have to fight back and challenge the Constitutionality of the order to lie. I won't give advice (IANAL, etc) but I think the most likely outcome would be a game of chicken. It would be a public fight (you have a right to a free and public trial with all evidence submitted in open, public court, obviously including the NSL or warrant!), and they'd risk an adverse judgement handing a tool to everyone to resist this.
So if they are willing to try you and admit the NSL or warrant as evidence, they are then revealing more than you have, and this undercuts their case.