The era of big data in astronomy lead to the application of machine learning techniques to large astronomical data sets. However, given peculiarities of astronomical data, machine learning models face a challenge due to a very expensive and time consuming labeling process. In this context, adaptive learning (or human-in-the-loop) techniques act as recommendations systems guiding the construction of optimal training sets. In this presentation, I will describe my efforts during the last ten, which were focus on developing adaptive learning environments for transient astronomy. Since this is an intrinsically interdisciplinary effort, such a narrative will cover the social context and history of the three main projects whithin which such efforts were implemented: COIN, SNAD and Fink.