Forcing the Liberated Soul to Deal with the Bitter Truth

Gemara: At the moment that they make a man enter his judgment [after his death], they ask him …

Ein Ayah: The extent to which one feels pain, whether physical or spiritual, such as fear, embarrassment, anguish, etc. depends on the degree to which matters are out of their proper norm, in the physical and/or the spiritual realm. One’s nervous system is prepared to be at ease when things are interwoven properly, but when things are out of place, there is pain commensurate to the deviation.
"Hashem made man straight" (Kohelet 7:29), and the spirit is prepared to receive feelings that fit its nature, such as security, honor, and happiness, as it does when things are in order. When matters are out of order, the soul experiences poison and bitterness, darkness and despair, as the suffering soul perceives it.
It is possible for a person to stray so far from a proper lifestyle that he no longer feels the pleasantness of following the divine ways of justice and uprightness. He also can stop feeling the pain that should result when one strays from the ways of justness. However, this forgetting of normalcy is not eternal. When the spirit is freed from the limitations of the body, which can lower the spirit to the lowest physical levels, it returns to its natural vigor and sensitivity and realizes that it is law and justice that form its natural order.
Man goes to his ultimate trial to be tried by himself, so to speak, as he becomes pained by the spiritual deficiencies and the abrogation of the Torah that he now uncovers. The spirit realizes with regret what it should have done and contrasts it with the evil of what he actually did. He finds that his level differs from the essence of the soul and from the whole of existence, which is all related to Hashem. It realizes the great potential that he, as a living person, possessed for wisdom, kindness, and justice and how he could have enveloped himself in justice and goodness had he properly followed the way of Torah and mitzvot. About this moment of realization we say that "man entered his ultimate trial."
A person who strayed significantly from the proper path to the point that he forgot his natural potential would rather stay in the dark about his potential than to have it held up before him. After all, the meeting with the truth causes great pain. That is the reason that divine powers have to force him to take part in his trial. However, Hashem, who is Master of All Souls, does not want man’s soul to be lowered forever, as it will eventually rebound from its lowliness and come back to positively encounter Hashem’s countenance. The spirit will return to the divine light after experiencing the bitterness of encountering the truth of its shortcomings. Thus, man will be brought into the trial according to his lofty level as a spirit without a body, not as a spirit sullied by the body. This is as Chazal tell us: "Against your will you are destined to come in judgment before the King of Kings, the Holy One Blessed Be He" (Avot, end of ch. 6).