From The Jedi Path by Daniel Wallace:
Trial of Insight Reveals a Jedi’s aptitude for distinguishing reality from illusion through deceptive challenges.
Can Jedi be deceived? Of course, but only if we ignore the will of the Force or the information in our Archives. A Jedi who is deceived is no longer working for the cause of the light side. In extreme cases, a Jedi operating under delusions may become a danger to innocents.
The Trial of Insight guards against this threat. It was the last test to be formalized as part of the Trials of Knighthood, and rose to prominence after it became clear that the Trials were producing Jedi who were brave, competent, and could overcome temptation–but who could not see through the patter of a simple con artist.
Deception and misdirection are threats to the Jedi, and our enemies frequently use them against us. The Hutts have been the ruin of countless Jedi campaigns throughout history, not due to their martial prowess but through their trickery. The Trial of Insight tests a Padawan’s ability to see through illusion and judge the person beneath, and to filter out distractions in search of the truth.
Over the centuries many challenges have been employed to assess this ability in the Trial of Insight. These include locating a single grain of sand within a field of stones, determining the content and meaning of a fragmentary text from scattered pieces, and solving any of the High Riddles of Dwartii–and no, researching the riddles in the Archives beforehand is not permitted.
The Trial of Insight may occur at a moment when you are not prepared for it, and may in fact be part of an unrelated challenge. I am reminded of three Padawans undergoing the eighth hour of the Trial of Skill. Through a perceptual trick all were made to believe they faced a horde of angry warriors. One battle on the face of certain defeat and passed her Trial of Courage. The second perceived the illusory nature of the combatants and passed his Trial of Insight. The third bowed out of the trial, citing exhaustion, and failed to become a Knight.
“Insight may also be gained by seeing beyond what is physically in front of you, to what is real.”
Of the five Trials, the Trial of Insight gives me the most issue when trying to come up with potential ways to test insight. As I have been told it has been done in the past, the deception has been done during the interview/trial process and has been done in increasingly disruptive ways. This does not settle well with me. With how draining the trials can be, especially with the Trial of Spirit, I feel like the student should be able to rely on the Jedi administering their trials. If a Jedi is the one to represent the Trial of Insight, I would rather it be one not otherwise involved with overseeing the trial. Not to say that there are ways it could be done ethically, but I see many problems.
I lean rather, to having someone not involved with the trial present the “deception.” Either a fellow Jedi not involved in the trial, or to have a scenario set up outside of the Jedi community, although this again proves the difficulty of having qualified individuals available for this.
As for the exact deceptions that could be used…it is difficult to say. While it would have to be something significant enough to register to the students sense of insight, I would also suggest that it not be something that causes a student deep distress.
A possible example that comes to mind is actually an April Fool’s joke some friends and I pulled on a friend back in High School. My friend was very much against smoking, so I acquired a pack of cigarettes from my older brother and my other friends and I acted as if we were going to go out back to “Smokers Corner” as it was known. Something like that could be done, to see if the Jedi figures out it is all a farce or if they believe their friends apparent actions. In fact, a good number of April Fool’s type ideas could work well for this.
A student could test out of the Trial of Insight if they have seen through significant deceptions before. For example, a deception I admittedly failed during my senior year of High School was being “quick changed” (in my defense, I was 17 years old and had only been a Jedi for about a year). Where a Jedi to encounter such a deception and see through it, that could warrant a pass on the Trial of Insight.