Courts and legislatures don't look too kindly upon flagrant violations of the spirit of the law. They view it as an end-run around their power. Although it happens slowly, loopholes do get shut (cf. Aereo).

A startup that's trying to get some notoriety in a few months or even years can definitely do something like this. Apple, who has to plan on a longer time horizon and who probably enlists the soft power of the government on a regular basis, has to be more cautious.

Something about that fact has always bothered me.

I can hire a team of lawyers and finance people to set up a complex system of subsidiaries so that my company only realizes profit in a specific way in a specific jurisdiction to avoid taxes, and as long as we've all followed the letter of the law, there doesn't seem to be any problem with the 'spirit of the law'. In fact, entire companies of accountants, lawyers and business consultants exist solely to help other companies follow the letter of the law while avoiding the spirit of it.

What makes it so that laws regarding anything "tech" get to be written and interpreted so vaguely and widely (from warrant canaries to copyright issues etc) when rules for everything from finance to oil spills are narrowly defined and interpreted?

I think that's actually a perverse case of survivor bias. You don't really get to be a significant oil or finance company without intimately knowing how to work with / play the regulatory system, so the ones you see still standing are the ones who really know how to capture the regulators. If you have an oil company worth $5 billion, you have figured out how to make regulators work for you.

Luckily, in the US at least, it's possible for a few nerds to build a company (say, Dropbox) that's as financially valuable as some long-established government schmoozers but has never thought about regulatory issues. So the "young" tech companies like Microsoft, Apple, Google, Facebook, etc. are less capable lobbyists on average.

I am not aware of any cases of warrant canaries being tested by the courts, but the general principle has been effective in the past in the UK.

When cars were first introduced, many towns across the UK viewed them as an opportunity to make money by fining the rich by setting obscenely low speed limits (think <20mph) with extraordinarily high fines. In response to this, the AA was formed to warn motorists of speed traps down the road.

This started to cut into profits, so the the government retaliated by charging and convicting an AA guy with "obstruction of justice". AA agents were therefore not allowed to inform motorists of speed traps.

The AA responded by changing their protocol. They would always salute passing motorists unless there was something wrong (aka, unless there was a speed trap). The absence of a salute indicated a speed trap, and the law could not force the AA to salute.

I'm not sure if this was ever challenged in court, but they were able to keep it up for several decades so it was never successfully challenged in court at least.

Edit: The AA could be considered sort of similar to the american AAA ("triple-A"). http://en.wikipedia.org/wiki/The_Automobile_Association http://www.theaa.com/aboutaa/history.html#tabview=tab1

I believe that this remained the habit of motorcyclists until relatively recently and it has since been tested in court and declared not allow (reference vague memories of newspaper articles).

On motorcycles, we put a hand on the helmet, signifying "man-with-a-hat ahead".

Do motorcyclists signal to others except when there is a speed trap, or do they signal to others when there is a speed trap? The later is common in the states (cars flashing their headlights), but I haven't heard of the former and enforcing a ban on it seems completely impractical at the very least.

And what kind of free society can force citizens to salute? "The government won't tolerate warrant canaries" makes intuitive sense because we have grown used to the courts throwing out all sensibility whenever there are computers involved, but the idea of the government compelling civilians to salute "in meatspace" seems blatantly beyond the pale.

We tap our helmets to warn of cops. We wave (or nod in countries that drive on the left) just to say hi. Absence of a signal would be useless on a bike as we're generally pretty bad about giving the signals we intend to give, let alone not giving the ones we don't intend to. It would be chaos.

What's AA?

The Automobile Association - Britain's equivalent to AAA in the US.

Applying that to the individual user level is probably too specific to slip past gag orders like this more general language is.

Then you download a 3rd party plugin that hides the message, and displays a big warning if it's missing.

Mainly because the .0000001% if apple users who actually care about this vs. the amount of work to implement isnt worth it business wise.