The advantages of Usage-Based Insurance for automotive covers over conventional rating methods have been discussed in literature for over four decades. Notwithstanding their adoption in insurance markets has been slow. This paper seeks to establish the viability of introducing fleet Telematics-Based Insurance by investigating the perceptions of insurance operators, tracking service providers and corporate fleet owners. At its core, the study involves a SWOT-analysis to appraise Telematics-Based Insurance against conventional premium rating systems. Twenty five key stakeholders in Malta, a country with an insurance industry that represents others in microcosm, were interviewed to develop our analysis. We assert that local insurers have interests in such insurance schemes as enhanced fleet management and monitoring translate into an improved insurance risk. The findings presented here have implications for all stakeholders as we argue that telematics enhance fleet management, TBI improves risk management for insurers and adoption of this technology is dependent on telematics providers increasing the perceived control by insurers over managing this technology.