While robot-assisted arm and hand training after stroke allows for intensive task-oriented practice, it has provided only limited additional benefit over dose-matched physiotherapy up to now. These rehabilitation devices are possibly too supportive during the exercises. Neurophysiological signals might be one way of avoiding slacking and providing robotic support only when the brain is particularly responsive to peripheral input. We tested the feasibility of three-dimensional robotic assistance for reaching movements with a multi-joint exoskeleton during motor imagery (MI)-related desynchronization of sensorimotor oscillations in the β-band. We also registered task-related network changes of cortical functional connectivity by electroencephalography via the imaginary part of the coherence function. Healthy subjects and stroke survivors showed similar patterns—but different aptitudes—of controlling the robotic movement. All participants in this pilot study with nine healthy subjects and two stroke patients achieved their maximum performance during the early stages of the task. Robotic control was significantly higher and less variable when proprioceptive feedback was provided in addition to visual feedback, i.e., when the orthosis was actually attached to the subject’s arm during the task. A distributed cortical network of task-related coherent activity in the θ-band showed significant differences between healthy subjects and stroke patients as well as between early and late periods of the task. Brain-robot interfaces (BRIs) may successfully link three-dimensional robotic training to the participants’ efforts and allow for task-oriented practice of activities of daily living with a physiologically controlled multi-joint exoskeleton. Changes of cortical physiology during the task might also help to make subject-specific adjustments of task difficulty and guide adjunct interventions to facilitate motor learning for functional restoration, a proposal that warrants further investigation in a larger cohort of stroke patients.