Tractor rollover is the main cause of both fatal and non-fatal injuries in agriculture. The foldable rollover protective structure (FROPS) can help to prevent these injuries. However, in many cases, the FROPS is left in a folded-down position. Human factor and rear-mounted FROPS technical characteristics influence operators’ behavior in roll-bar handling. To improve the FROPS’s comfortable use, the prototype of an enhanced handling system was developed, and its usability was tested and compared with a conventional FROPS. Usability was assessed with 93 novice tractor users through an ad hoc questionnaire (investigating perceived effort, time demand, the posture adopted and satisfaction) and observations (investigating effectiveness and efficiency) during lowering and raising tasks. For both tasks, the participants perceived significantly less effort, less physical discomfort, a higher level of satisfaction and less time demand while operating the enhanced FROPS. Observations showed that the critical issues that emerged for the conventional FROPS were eliminated by adopting the developed and implemented handling system. The developed handling system showed itself to be usable and effective in making the FROPS easier and safer to be operated.