The fact that I have to listen to a "your call may be monitored" spiel every time I talk to customer support leads me to believe tech should at least be annoying on first boot if never again.

That you link an investigative Wired article shows that most people aren't going to know this information. Siri users aren't all 2013 Wired readers, nor are they waiting around to hear what an Apple spokesperson is going to clarify.

Frankly, Apple should at least prompt people even just to be the good guy when it comes to privacy fallout on all these services.

You get a separate pop up to enable Siri. I read it and said no.

Granted, that might not seem like enough, but it was clear enough IMO.

No, I agree that if the "your call may be monitored" is played before every monitored call centre phone call, then Siri should also remind people, at least once every other day. I'm not sure how often people reboot their iPhones, but I don't think doing it just on boot is enough, either.

It would drive the point home if Siri just said, every N queries, "anything you say to me can and will be sent to Apple's servers for analysis purposes".

Call centers don’t know who is calling, and thus add the message every time. It’s essentially always the first message until you identify yourself.

As to regular pop ups or messages, that’s simply a worse user experience for zero benefit.