Augustine, the fourth-century Christian philosopher and theologian, is perhaps best-known for his account of his spiritual journey in "Confessions". Two aspects of the problem of evil are arguably critical for comprehending his life in Books 1 through 9 of the work. His search for the nature and origin of evil in the various philosophies that he encounters (the intellectual aspect) and his struggles with his own weaknesses (the experiential aspect) are windows for understanding the actual dynamics of his sojourn. Examining relevant events from Augustine’s life chronologically, the analysis here follows his philosophical wanderings from his encounter with Cicero’s "Hortensius" through his eventual disillusionment with the Manichaean religion, and finally, his move in the direction of Christian teachings with the help of Neo-Platonism. During his journey his intellectual quest and the personal battle with his own depravity impact each other until his ultimate move toward Christianity resolves both struggles.