Abstract: To advance automated apple harvesting through human-machine collaboration, this study investigates user interactions with a soft, wearable haptic device designed for future cyber-physical systems (CPS). Haptic interfaces provide tactile feedback (vibration, pressure, and/or temperature) to create a more immersive and informative user experience. This haptic device utilizes heat-sealed inflatable fabric pouches to apply normal force to the user’s wrist, supporting improved real-time teleoperation and situational awareness. Such feedback allows for intuitive, non-visual guidance and helps reduce operational errors during remote tasks. This work also examines the development of an untethered version of the device, designed to enhance mobility and practical deployment. The device will then be integrated into a remotely teleoperated system, to guide users to a targeted fruit. Overall, this work contributes to the design of intuitive wearable haptic devices, demonstrating the potential of soft pneumatic actuation for delivering directional and location-specific feedback, while also validating the feasibility of untethered operation without compromising performance.