Augustine, the fourth-century Christian philosopher, is perhaps best-known for his spiritual autobiography 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. I defend the idea above by providing a fuller examination of the key role that both aspects play in his spiritual journey. Examining relevant events from Augustine's life chronologically, I analyze his philosophical wanderings from his encounter with Cicero's work 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. Along the way his philosophical questions (the intellectual aspect) and his struggles with his own depravity (the experiential aspect) have an effect on each other until his ultimate move toward Christianity resolves both problems of evil.