This is considered the earliest of Augustine's writings (composed circa 386 CE in Cassiciacum). It is of great historical interest in relationship to the study of the Platonic Academy, Stoicism, Cicero and Ancient Skepticism in general as well as offering some hints regarding Pythagoreanism and Augustine's relationship to Plato and Plotinus (mentioned explicitly as being almost an reincarnation of Plato), not to mention the strange oblique references to Christianity (described in the language of the mysteries - Augustine was supposedly undergoing the preparations for the "initiation" of baptism which he was to receive a year later). The Christian references may be later interpolations just as the historical-biographical setting of the dialogue could well be a purely rhetorical and literary device (serving a political goal).
In Book III Augustine articulates what can be described as a theory of analyticity. Concrete instantiations of logical propositions are held up as certain and evident truths. And these "logical" propositions are equated to truths of "dialectics" and they appear to be Stoic in form (conditionals and disjunctives). In the same book he likewise articulates the theory of self-certifying evidences in the context of phenomenological epokhê. The perceptive experiences of consciousness - provided they are considered merely as such by suspension or exclusion of further judgment (assent) - are indubitable certain. Augustine thus genuinely effected the transcendental reduction whereby the primordial certainty and truth of the world is that of a system of phenomena (for a given subject) indistinguishable in this respect from dreams. In III.11.25 we read quidquid tale mihi videtur, mundum appello. We could also compare Clitomachus' distinction between assent and approval (cf. Ac.2.104) with key aspects of later phenomenology. The dialogue has a close connection to Cicero's (fragmentary) work Academica and the sections on the ultimate aims and nature of the later Academy's skeptical stance are of supreme interest and importance. Note that Augustine had access to the full versions of this work. It suggests that the function of the dialectics of Arcesilaus and Carneades was as a "skillful means" directed at a materialist versions of Stoicism having as ultimate aim the preparation for receiving the Platonic philosophy - and this is in perfect agreement with the function of Nagârjuna's Madhyamaka or its later Vedantic version. There is however not a hint of this interpretation in Charles Brittain's introduction to his translation of the Academica (2006). Brittain expounds a humdrum interpretation of Philo and Antiochus in terms of fallibilism and defeasibility. However it seems plausible that it is in the so-called Megarian school (alongside Sextus) that the purest form of Western Madhyamaka (i.e. the highest articulation of dialectics) is to be sought (cf. the description of Arcesilaus in Diogenes Laertius: Plato in front, Pyrrho behind and Diodorus in the middle). We can find much phenomenological psychology in the later Academy and Stoics.
The major questions which we should answer are the following. What are the historical sources for Augustine's anti-skeptical argument involving the appeal to the certainty of validities of Stoic propositional logic? While such an argument permeates the Platonic dialogues it is to us unthinkable that the great logician Chrysippus would not have used such arguments in his innumerable debates with the later Academy. The "phenomenological" argument can be traced back to the Pyrrhonist epokhê, Epicurus' pasa aisthesis estin alethes, and to a certain extent to Protagoras - but differs significantly from the Stoic theory of kataleptike phantasia. Note that we have argued that this kind of experiential epokhê is found clearly attested in the Pali Nikayas (and the sophisticated development in the Yogãcãra school). A curious fact about the Contra Academicos is that Augustine's famous argument si fallor, sum (Civ. Dei XI. 26, De Trin. X.10.14 ) is entirely absent despite there being ample opportunity to introduce it. While it is highly plausible that Augustine drew this argument from Cicero's Hortensius or other material (cf. Plotinus' treatment of second-order awareness or parakolouthēsis) , we note that this argument also appears in Shankara's commentary on the Brahma Sutras as well as several other earlier and later texts in Indian philosophical schools.

