Nor, of course, are we smart enough to contemplate all the various ways in which we might "fail" and so we are unable to practice for every type of failure -- which means that, in fact, we WILL be "Experiencing a specific failure for the first time in a real life environment..." and we can only hope that our general training has prepared us to cope with some specific failure/incident.
HOWEVER -- back to one of the original questions, What SPECIFIC FAILURES have you, as a technical diver, actually faced -- and bonus question, how did your scenario based training match up with what actually happened?
In my experience, the most dangerous failure is what I call "The Smug Alert" failure named after the South Park episode that inspired it. It happens when divers start to feel really good about their training and experience and become lost in a cloud of smug that reduces visualization and the ability to respect all dives, no matter how benign, as "real" and potentially life-threatening.