Theory testing within small-N research designs is generally considered problematic. Developments in the philosophy of social science have opened up new methodological possibilities through, among other things, a novel notion of contingent causality that allows for contextualized hypothesis generation, hypothesis testing and refinement, and generalization. This article looks to contribute to the literature by providing an example of critical realist (one such new development in the philosophy of social science) research on a small-N comparative case study that includes hypothesis testing. The article begins with the key ontological assumptions of critical realism and its relation to theory and explanation. Then, the paper presents an illustrative example of an e-government and trust comparative case study following these ontological assumptions. Given word length limitations, the focus of the example is on the nature and process of theory and hypothesis development, rather than the actually testing that occurred. Essential to developing testable hypotheses is the generation of tightly linked middle-range and case-specific theories that provide propositions that can be tested and refined. The link provides a pathway to feedback the concrete empirical data to the higher level (more abstract) and generalizable middle-range theories.