The adjunctive use of biofeedback systems with exoskeletons may accelerate post-stroke gait rehabilitation. Wearable patient-oriented human-robot interaction-based biofeedback is proposed to improve patient-exoskeleton compliance regarding the interaction torque’s direction (joint motion strategy) and magnitude (user participation strategy) through auditory and vibrotactile cues during assisted gait training, respectively. Parallel physiotherapist-oriented strategies are also proposed such that physiotherapists can follow in real-time a patient’s motor performance towards effective involvement during training. A preliminary pre-post controlled study was conducted with eight healthy participants to conclude about the biofeedback’s efficacy during gait training driven by an ankle-foot exoskeleton and guided by a technical person. For the study group, performance related to the interaction torque’s direction increased during (p-value = 0.07) and after (p-value = 0.07) joint motion training. Further, the performance regarding the interaction torque’s magnitude significantly increased during (p-value = 0.03) and after (p-value = 68.59×10-3) user participation training. The experimental group and a technical person reported promising usability of the biofeedback and highlighted the importance of the timely cues from physiotherapist-oriented strategies. Less significant improvements in patient–exoskeleton compliance were observed in the control group. The overall findings suggest that the proposed biofeedback was able to improve the participant-exoskeleton compliance by enhancing human-robot interaction; thus, it may be a powerful tool to accelerate post-stroke ankle-foot deformity recovery.