6) Entering my account information on an automated call system only to be asked it again when a human finally picks up.

Being on the other side of this system, and hearing *BEEP* *BEEP* *BEEP* *BEEP* *BEEP* *BEEP* *BEEP* *BEEP* *BEEP* *BEEP* due to one little macro screwup, and knowing those beeps represented the phone number needed to look up the info.