This article elaborates on how structural, normative and functional pressures for change may challenge military organizational characteristics. We problematize theoretically and exemplify empirically what consequences these pressures can have on military organizational characteristics, arguing that they constitute major challenges for managing in particular normative pressures for change. The empirical examples suggest that bureaucratic, hierarchical, narcissistic and greedy traits of the organization are challenged by normative pressures such as value changes and normalization. Another source of challenge is professionalization processes. Structural challenges, on the other hand, are managed by the organization and do not seem to inhibit the workings of organizational characteristics. The plausibility probe conducted questions the sustainability of military organizational characteristics in their traditional disguise, in particular due to legitimacy concerns. It is suggested that future research should be directed towards analyzing how military organizations manage pressure for change and whether their characteristics are questioned.