This article is presenting an overview of the literature devoted to entrepreneurial learning and, more specifically, those research bringing environmental elements into the study of the entrepreneurial learning process. Then, it shows how each of the four Special Issue selected research papers contribute to enhancing our knowledge of the complexity of the learning process vis-à-vis entrepreneurial processes placed in context. By doing this, it makes an attempt to explain the specific context behind each contribution as well as presenting the wider context. Finally, the article is suggesting a set of key challenges and research pathways that might be explored in the future.