This research aims at developing path and motion planning algorithms for a tethered Unmanned Aerial Vehicle (UAV) to visually assist a teleoperated primary robot in unstructured or confined environments. The emerging state of the practice for nuclear operations, bomb squad, disaster robots, and other domains with novel tasks or highly occluded environments is to use two robots, a primary and a secondary that acts as a visual assistant to overcome the perceptual limitations of the sensors by providing an external viewpoint. However, the benefits of using an assistant have been limited for at least three reasons: (1) users tend to choose suboptimal viewpoints, (2) only ground robot assistants are considered, ignoring the rapid evolution of small unmanned aerial systems for indoor flying, (3) introducing a whole crew for the second teleoperated robot is not cost effective, may introduce further teamwork demands, and therefore could lead to miscommunication. This dissertation proposes to use an autonomous tethered aerial visual assistant to replace the secondary robot and its operating crew. Along with a pre-established theory of viewpoint quality based on affordances, this dissertation aims at defining and representing robot motion risk in unstructured or confined environments. Based on those theories, a novel high level path planning algorithm is developed to enable risk-aware planning, which balances the tradeoff between viewpoint quality and motion risk in order to provide safe and trustworthy visual assistance flight. The planned flight trajectory is then realized on a tethered UAV platform. The perception and actuation are tailored to fit the tethered agent in the form of a low level motion suite, including a novel tether-based localization model with negligible computational overhead, motion primitives for the tethered airframe based on position and velocity control, and two different