Although scholarship ebbs and flows in its sense of how likely it is that the author of Hebrews knew of Philo, both of these authors attest to certain common mechanisms by which they connected Jewish Scriptural texts to each other. This paper explores techniques Hebrews and Philo held in common and analyzes their similarities and differences. First, the paper shows that Hebrews and Philo seemed to have used a similar text of the LXX at a number of idiosyncratic points. Second, it shows that they both often used a secondary text to reinforce or develop the putative meaning of a primary text. The remainder of the paper analyzes three similar exegetical techniques they both arguably used to connect Scriptures together. Both use exempla from the Jewish Scriptures with commonly perceived characteristics to reinforce a point. Hebrews 11 is an obvious example for Hebrews. Philo's lengthy discussion of Genesis 3:14-15 in his Allegorical Interpretation also provides several examples of such exempla. Both Hebrews and Philo connect texts to each other on the basis of catchwords (gezera shawa). Hebrews 4:1-11 is an obvious example of connecting Psalm 95 to Genesis 2:2 based on the word "rest." The same section of Philo's Allegorical Interpretation has an example of such a connection made on the basis of being cursed (Leg. All. 3:107). Most of Philo's connections, however, are made on the basis of some deeper, more allegorical connection between what he perceives to be the deeper meaning of one passage and that of another. He uses the etymologies of names, for example, to discover deep meanings he can connect to the deep meanings of other passages. He does this with the name of Noah and Melchizedek and Bezalel in the same section of the Allegorical Commentary mentioned above. Interestingly, many of the passages Philo links together in this section are also passages that appear throughout Hebrews. Hebrews is not averse to such interpretive techniques (e.g., 7:1-3), although it uses them more to interpret individual passages than to connect passages in the Jewish Scripture to each other. Hebrews thus sticks a little closer to the surface of texts when making connections than Philo, whose connections more often are allegorical. Hebrews uses allegorical interpretation, just not so much in the connection of scriptural texts. The paper concludes by noting again the striking amount of similarity between Hebrews and Philo just on this one topic alone just in one section in Philo. It corroborates again the sense that, whether the author of Hebrews knew Philo's works or not, the two individuals surely swam in very similar Diaspora waters.