So the FBI was not able to force the Canary update? Maybe the criminals are not so savvy as to even know what a Canary is so the FBI didn't care?
My suspicion is that Canaries would not necessarily survive a legal challenge, as courts are able to enforce the intent of their orders fairly widely (and if you refused to comply that would be contempt). The US does have the protections against compelled speech, but I wouldn't like to test constitutional protections given what's been happening. My feeling is that to make this compulsion happen though, it would raise the risks (to LE) in doing so, so they held off it. If it came to light (it would eventually), then the obvious response is for many providers to immediately go outside jurisdiction. I know I'd have that as a warm contingency if I were operating a service like that. The idea that criminals are not savvy doesn't match the evidence, even granted the naive or careless (who get caught), I suspect they are often stooges and fall-guys.
Well, I knew that they had received a gag order, because of this tweet: But I didn't care. Because I use VPNs, and encrypt sensitive stuff. And because I'm not trying to hide metadata, using Riseup.