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Emerging aviation markets such as urban air mobility are giving rise to new technologies and means of operation. However, novelty may hide ‘unknown unknowns,’ raising new hazards. This paper examines how expertise and safety techniques enable transformative technologies such as reduced crew operations, hybrid wing-borne and rotor-born flight, federated air traffic services, and urban operations. We explore how analysts use expertise to address common-cause failures, collect and interpret safety data, and perform exacting tradeoffs between dissimilarity, redundancy, independence, and diversity (human, process lifecycle, or otherwise) to ensure safety. When novelty is present, analysts might not possess the expertise needed to fully understand the implications of design decisions and tradeoffs being made, especially in early lifecycle phases, on emergent properties such as safety. Safety expertise must be carefully cultivated. The conflicting views of safety experts must be unpacked to identify the divergence in fundamental assumptions, models, means, and methods that may be causing them. Once systems venture beyond the basis of what safety expertise can reliably guarantee, projects take on risk that must be managed. The paper contains key takeaways and actionable recommendations for novel OEMs and regulators touching on topics such as robust monitoring; clear and transparent reporting; incremental approaches to fielding novel systems in hazard-rich, risk-tolerant environments; the cultivation of safety culture and expertise in an organization; and the use of scientific study to reduce epistemic uncertainty in novel operations with new technologies. Since excessive novelty in aviation can undermine the current foundation of safety, humility and incrementalism are necessary to enable emerging aviation markets safely.