Cooperation between road users based on V2X communication has the potential to make road traffic safer and more efficient. The exchange of information enables the cooperative orchestration of critical traffic situations, such as truck overtaking maneuvers on freeways. With the benefit of such a system, questions arise concerning system failure or the abrupt and unexpected behavior of road users. A human-machine interface (HMI) organizes and negotiates the cooperation between drivers and maintains smooth interaction, trust, and system acceptance, even in the case of a possible system failure. A study was conducted with 30 truck drivers on a dynamic truck driving simulator to analyze the negotiation of cooperation requests and the reaction of truck drivers to potential system failures. The results show that an automated cooperation request does not translate into a significantly higher cooperation success rate. System failures in cooperative truck passing maneuvers are not considered critical by truck drivers in this simulated environment. The next step in the development process is to investigate how the success rate of truck overtaking maneuvers on freeways can be further increased as well as the implementation of the system in a real vehicle to investigate the reaction behavior of truck drivers in case of system failures in a real environment.