We explore individuals who take some of their technology use ‘underground’, described as ‘bootlegging’, to enhance healthcare work. We find that healthcare professionals’ informal use of mobile applications in healthcare work sometimes ‘sticks out’ and this produces professional identity tensions: (1) conflict with perceptions of professional behaviour, and (2) defilement of expert judgment. Our analysis, moreover, reveals that identity work (i.e. ‘accepting’ and ‘sensemaking’) provides a coping mechanism to deal with these unresolved professional identity tensions. This paper contributes to a better understanding of the constitutive entanglements and two-way interactions of discretionary technology bootlegging, professional identity and autonomy in institutional healthcare work.