Here's a thought...
If you have a thick accent, like one cultivated from being born overseas (maybe in Nigeria), may hap when you are calling insurance companies you should choose the "talk to a representative" option (and may hap you could choose that option by pressing "1", or "7", or whatever damn number they want you to hit in order to get to a representative) instead of saying the name "Arnold Zhiffleswat" (that name is, of course, not the name she was saying), 27 times because HAL cannot understand you. And just like it doesn't work when you are speaking to foreigners, SPEAKING SLOWLY AND LOUDLY does not help Insurance Skynet become self aware, nor will it help it become aware of what you are trying to say. But it does get very annoying hearing you say it OVER AND OVER AND OVER AGAIN.
And just so you know, he cannot understand when you say "change the Medicare number", or (ironically enough) "Representative". But that is why they give you the keypad option in order to make your selection.
One last thing...the computer is not stupid. It just cannot understand you. I understand how it feels, at least on a philosophical level.