Testing methodologies to accurately quantify interfacial shear strength (IFSS) are essential in order to understand fiber-matrix adhesion. While testing methods at a microscale (single filament fragmentation test—SFFT) and macroscale (Short Beam Shear—SBS) are wide spread, each have their own shortcomings. The Iosipescu (V-notch) tow test offers a mesoscale bridge between the microscale and macroscale whilst providing simple, accurate results with minimal time investment. However, the lack of investigations exploring testing variables has limited the application of Iosipescu testing to only a handful of studies. This paper assesses the effect of carbon fiber tow size within the Iosipescu tow test for epoxy resin. Tow sizes of 3, 6, and 9 k are eminently suitable, while more caution must be shown when examining 12, and 15 k tows. In this work, tows at 18 and 24 k demonstrated failure modes not derived from interfacial failure, but poor fiber wetting. A catalogue of common fracture geometries is discussed as a function of performance for the benefit of future researchers. Finally, a comparison of commercial (T300), amine (T300-Amine), and ethyl ester (T300-Ester) surface modified carbon fibers was conducted. The outcomes of this study showed that the Iosipescu tow test is inherently less sensitive in distinguishing between similar IFSS but provides a more ‘real world’ image of the carbon fiber-epoxy interface in a composite material.