Siri is actually a dimmed down version of the 90’s chatterbots
A long time ago, in the 60’s to be exact, a guy by the name of Joseph Weizenbaum created AIML. This was a superset of XML that allowed a simple algorithm to go trough a tree of choices and pattern match the best answer, giving the impression that it had a sort of intelligence to it. Obviously, it didn’t. It was more or less a supercharged switch statement.
Later, in the 90’s, AIML the next big thing :)
There where hundreds of different online and offline chatter bots . You could actually build your own; The way it would work is that you would set up this kind of “AI” on a Yahoo Messenger or IRC and than you needed to teach it different response patterns.
The more you would interact with it, the more it would learn different topics and appear smarter. Of course there was software that could allow you to build this kind of dictionary files, some of the chatter bots could be quite “smart”. One example that is still online today is CleverBot.
Now back to the pressing matter.
Sir ( and other bots like Cortana ) is a stripped down version of Eliza with some of the features removed. Features like: learning /topics / advanced patterns and so on. There is a reason for that. Apple doesn’t want or need users to teach it’s chatter bot things, people can be assholes, and as far as topics and other advance features are concerned, who would want to have a full conversation with their phone while making an appointment?
So the only new features seams to be contextual information and live widgets. Think about the time google suggested you leave early because there is a traffic jam or when Siri pasted the whether information on your lockscreen. This are not big improvements, actually, from a technical perspective, this things are quite simple.
So, no, the chatter bots are not getting any smarter. Siri is closer to a smart door lock than to Ava from Ex Machina and, regardless of what apple is marketing, it is not “learning from your behavior” or even have the ability to do so ( except for some targeted ads code probably in there somewhere ) …
Like a lot of tech stuff this days, Siri is just a repackaging of an old technology so that it is more consumer friendly and brings the younger crowd in. Fact of the matter is that we are no closer to intelligent chat bots now then we were in the 60’s .
If you want to learn how to develop your own Siri, here are some links to get you started: