Automation has been long explored to improve regulatory compliance during building design. Despite substantial research efforts on developing means to enable this process, there has been limited success in practical implementations. Designers’ inputs are often undervalued in such developments, leading to solutions that are not effectively incorporated into the design process. This issue is even more difficult in healthcare projects due to their complexity and convoluted regulatory frameworks. In this paper, we describe how designers perceive the use of automation to support regulatory compliance in healthcare projects, through the analysis of a series of semi-structured interviews. We found that regulatory documents have a large influence on design and their compliance often consists of an unformalized process in practice. Furthermore, we identified that subjectivity is perceived in requirements as needed due to the creativity involved in design, whereas automation can be understood as liberating in this context depending on how it is used. Improvement needs focusing on the revision of the regulatory framework as well as on software development have been highlighted by participants during the interviews, which led to the proposition of recommendations to help achieve their benefits in practice.