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This paper presents the preliminary findings of an anonymous web-based survey addresing pilot work related stress (WRS) and wellbeing. The initial analysis indicates that pilots are under stress and experiencing wellbeing problems. Specific features of the job can result in wellbeing problems, spanning the three pillars of wellbeing. Critically, sources of WRS can increase a pilot’s risk in terms of developing a mental health (MH) issue. Further, sources of WRS can impact on performance and safety. Considerable barriers still remain in relation to reporting MH issues at work. Coping mechanisms addressing sleep/fatigue, diet, exercise and communication/reporting, enable some pilots to thrive in an environment that has negative impacts for others. The vast majority of pilots indicated that issues pertaining to WRS and wellbeing are not being adequately managed in terms of airline safety management systems/processes. Potentially, airline interventions might focus on enhancing existing safety management system processes/technology to address risks associated with WRS and wellbeing, training pilots, and introducing new wellbeing briefing/reporting systems. Further, new digital tools might be advanced to support pilot self management of WRS/wellbeing and risk identification, both inside and outside work.