This paper investigates one of the essential topics of Islamic spirituality which is self-knowledge and its relationship to divine trial and tribulation. Knowledge of the soul has been the focal point for Islamic philosophers, mystics and sages as they have included it in every discussion on spirituality. Self-Knowledge constitutes knowing how to discipline and transform the soul, and thereafter actualize the higher human faculties of the heart and intellect. Because the soul is allusive and recalcitrant by nature, spiritual teachers have devised various stratagems to discipline and rectify it. There are two aspects to that training: human and divine. On the human side, one disciplines himself through the intellectual faculty and/or is trained by an expert who is considered the spiritual physician, Shaykh or sage. On the divine side, God is the teacher who trains His servant through bounties or trials. The trial is the mirror, or the reality-check through which the believer sees his own soul, rectifies his behavior and awakens to God-consciousness. The divine trial may extend beyond the individual as in the case of a pandemic, often giving rise to a global awakening. Learning lessons through divine trial has many aspects, the most salient of which will be covered in this paper.