Supporting eyes-free interaction, mobility and encumbrance, while providing a broad set of commands on a smartwatch display is a difficult, yet important, task. Bezel-to-bezel (B2B) gestures are valuable for rapid command invocation during eyes-free operation, however we lack knowledge regarding B2B interactions on circular devices during common usage scenarios. We aim to improve our understanding of the dynamics of B2B interactions in these scenarios by conducting two studies and a third analysis: First, we explore the performance of B2B in a seated position; second, we explore the effect of mobility and encumbrance on the B2B interaction; finally, we improve on the B2B accuracies by calculating features and utilizing machine learning. With the limited interaction capabilities on smartwatches and the importance of the scenario of use, we conclude with applications and design guidelines for improved utilization of B2B that enables effective smartwatch control while in common, mobile and eyes-free scenarios.