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Single Pilot Operations (SPO) represent a viable concept for commercial aviation in near future. It will require different training regimes to contemporary airliners’ pilots because the single-pilot’s and remote operator’s (including the dispatcher’s) responsibilities and accompanying procedures will change, both in air and on ground. This initial system-theoretic analysis of suggestions for training of single pilot and remote-copilot identified the agreement of job rotation of both. Hence, pilots can still be trained in new single-pilot specific procedures in a special training fleet to includes the apprenticeship-style training in SPO. Advanced new automation tools will be challenging to be included into training. On this basis, skill degradation becomes an issue and must be solved. Nonetheless, the training issue can be early tackled by applying worker competencies’ analyses when investigating different concepts in depth early in the design process of SPO.