In his work, Philo frequently introduces a juxtaposition of two texts, texts that highlight a tension within his understanding of the Divine: that “God is not like a human” (Num 23:19) and yet that “like humans disciplines their children, so God disciplines you” (Deut. 8:5). The apparent contradiction between these verses sums up Philo’s presuppositions of God’s utter transcendence and of God’s guidance of humanity toward perfection. Philo overcomes this conceptual tension primarily through relying on the Greco-Roman concept of “pedagogical adaptability,” a disposition that involves a teacher or guide adapting to individuals’ abilities and needs to lead them on in maturity or virtue. “Adaptability” does not come in Philo’s writing as a foreign imposition on Israel’s Scriptures, however, but serves as an explanation as to why, for example, the utterly transcendent God is portrayed as changing his mind, moving in space, or saying something not appropriate to divine dignity: God allows such indecent descriptions as a temporary concession to human weakness. This paper, then, identifies the ways in which Philo’s (Hellenistic) philosophical framework and his commitment to Israel’s Scriptures create the theological tension between transcendence and humanity’s need for divine instruction, and yet how those two commitments also provide him the means to resolve this same problem via “adaptability.” I describe briefly “adaptability” as those in Philo’s world employed the notion, and show the various ways Philo himself puts this concept to work, especially by means of his Logos theology. Specifically, I show how Philo seems to draw upon this concept prevalent among his philosophical forbears and contemporaries. To illustrate this argument, I analyze Philo’s De mutatione nominum (esp. 1-26) and De somniis (esp. 1.231-239). In the introduction to the first work, Philo explains how it is that the human mind can possibly perceive the imperceptible God, how humans can even speak of God, and how God’s divine agents—“the Lord” and “God”—both serve as guides for feeble humanity to ascend toward greater virtue. Ultimately, Philo believes all of these accommodations to human weakness and limitations allow the earth-bound soul to ascend to mystical union with God. In De somniis, Philo regards the actions of the various agents of God, of whom the Logos is chief, as means of divine-human interaction that simultaneously maintains divine transcendence, yet also enables humanity to improve in virtue. Taken together, De mutatione and De somniis exemplify Philo’s awareness of God’s pedagogical accommodation to humanity, an act drawing upon both his philosophical commitments and the his interpretation of Jewish Scripture.