This paper contributes to the IS misfits and workarounds literature by demonstrating how “work system–technology” misfits and workarounds can be mutually related. In the context of electronic health record (EHR) systems, this study examines when misfits experienced between an EHR system and health professionals' work practices lead to workarounds with negative consequences in terms of aggravating misfits. Our qualitative study was conducted in two tertiary hospitals in The Netherlands that had implemented an off‐the‐shelf EHR system. We analysed the “misfit experience → response → consequence” sequences that emerged from interviews complemented with observations and documents. Experienced misfits between the EHR and other work system components induced highly varied responses, among which workarounds. While workarounds can be beneficial, we found occasions where workarounds resulted in aggravated misfits. We conceptualise three underlying misfit‐aggravating EHR‐use patterns emerging from (1) a non‐routine practice's perceived exceptionality, (2) collective separatism in incompatible routine practices, and (3) individual deviancy in routine work practices. These patterns differ in terms of the work practices' routineness, professionals' misfit experiences, and in how this combination provokes an individual or collective workaround that is non‐compliant with both the designed technology use and the organisational intent. To understand how these patterns emerge, we discuss the interplay among work practice routineness, misfit characteristics, and non‐compliant workaround behaviours.