Due to the low ratio of medical decisions made upon solid scientific evidence (4%) and the low efficiency of deploying knowledge in practice (17 years), the concept of a learning health system (LHS) was initiated to speed up knowledge generation and adoption and systematically approach continuous improvement in clinical practice. This concept can be illustrated by a so-called learning health cycle. This cycle, the first version as well as its variants, provides a framework for discussion on a common basis and has been well-accepted by the medical communities. Though the idea attracted major attention widely, very little has been done in way of actual adoption in real practices in the past 10 years. Nevertheless, as one of the pioneers in Taiwan, we have been involved in the effort to implement the LHS locally since 2016. In this article, we systematically summarize the evolution of the learning health cycle, review cases of its applications and briefly introduce the work we have done for promoting LHSs in Taiwan. Based on the experience we have gained, we try to identify the challenges and opportunities in Taiwan. While full-scale electronic medical records powered by the National Health Insurance system give Taiwan a special advantage in achieving a nationwide LHS, the medical community is not yet ready for a dramatic change. The lack of infrastructure for this use and motivation to take action right away makes the implementation of a LHS in Taiwan challenging.