The relation of philosophy to theology is notoriously ambiguous. Reading Philo of Alexandria is a case in point. Understanding the dynamics of philosophy and theology in the Philonic corpus is a key to understanding Philo's thought. And yet, few scholars agree as to how to read Philo on this point. In this article, I highlight some of the hermeneutical challenges posed by the Philonic corpus, based on two recent publications. The first book, a recently edited volume, documents the current trends in the discussion, introducing the reader to the 21st century scholarship. The second book, the first translation into English of an older monograph, echoes earlier trends, reaching back to the beginning of the previous century. Both publications complement each other, together covering a hundred years of Philonic scholarship. They thus offer a sound guide to the perplexed, even though they ultimately suggest alternative ways of reading Philo. In what follows, I argue that the perennial challenge of every Philo reader is to decipher Philo's enigmatic strategy in combining the Greek philosophical tradition with the Jewish scriptural tradition. To delve into this mystery, I submit, is the reason why Philo will continue to fascinate scholars for generations to come.