Earlier quoted context omitted.
Because that would get the company in trouble even a normal warrant to say nothing of the gag order on an NSL. It's too specific and tips off the exact people being investigated. The lawsuit the company would be hit with would be huge, expensive and a pretty straight forward loss.
I don't see why. It's the exact same principle as standard warrant canaries.
Canaries aren't challenged currently partially because they give out so little information that it's really not worth the governments time to go after people. What the NSL gag really aims to prevent is to keep the people targeted by the NSLs from knowing that they're under investigation. If a company started doing canaries that applied down to a single person they'd be sued the first time they stopped sending one after getting a letter.
Also I'm not entirely sure that even if a judge found that an NSL can't compel you to send a zombie canary that it follows that the company can't be fined or sanctioned for breaking the gag order.