The process of verifying the compliance of design solutions to regulations is critical in healthcare design due to the complexity of the requirements present in healthcare settings. The majority of previews research concentrates on "mistake-searching", assuming that design will not be compliant and, as such, necessitates an approach focussed on finding inconsistencies, rather than avoiding mistakes during the design process. This paper reports findings of an ongoing research that follows the Design Science Research approach, with the aim of exploring how existing technologies can support incorporating mistakeproofing (poka yoke) into healthcare design, framed within the regulations compliance process. A set of technological strategies was assessed according to mistakeproofing principles. The analysis evidenced their characteristics, benefits, limitations and examples of application. These technologies rely on the use of hybrid approaches, providing assistance to designers across all design stages, which in turn supports better decision-making and contributes towards improving value generation. A theoretical framework was proposed based on the synergy between design support systems, requirements subjectivity and jidoka. It highlights the importance of better understanding and enhancing the relationship between human designers and different technologies through automation.