E-bikes can significantly enhance adoption of cycling as an urban transportation mode and have the advantage of low space requirements, very small operational GHG emissions, and a negligible contribution to infrastructure degradation. This work explores some key environmental and physical performance features of E-bikes in real world settings in order to systematically determine the capabilities of E-bikes for greater adoption. This includes analysis on the lifecycle emissions associated with E-bikes and comparisons with other major urban modes. Empirical data was collected about the performance of a third-party electric motor technology that could improve energy efficiency. The ability of this technology to offer improvements under real world conditions was verified and showed promise with recommendations for further development. A trial of E-bikes deployed in a corporate fleet, with 17 riders and over 600 km of trip data was completed and used for several additional analyses. This include validating a mathematical model of an E-bike, as well as extending the boundaries of previous lifecycle research to include upstream dietary emissions associated with human supplied mechanical power while riding an E-bike. The results in this thesis show both the strengths of E-bikes as used for corporate and personal transportation, as well as the barriers that still remain for greater adoption.