Workplace learning has been part of our everyday reality since a long time, but at present, it has become more important than ever before. New technological opportunities can radically change not only formal, but also informal (unintentional) learning, typical for the workplace. Nowadays companies face a new challenge, which is the transition towards Industry 4.0. It is a complex process that concerns both executives and employees. Therefore, it is important to find solutions that make it easier for both sides. This change is accompanied by numerous re-qualification requirements, which demand a radical improvement of workplace learning and on-the-job training. Recent developments enable a more precise understanding of users’ needs, which can lead to better personalization of learning experiences. The effectiveness and efficiency of training and work processes can be improved through wearable technologies and augmented reality. Information technology should support the whole spectrum of educational methodologies, including personalized guidance, collaborative learning, and training of practical skills, as well as meta-cognitive scaffolding. Here we provide a reflective view on the former progress of adaptive workplace learning assistance (especially in the European context) and then point out several prospective approaches that aim to address the current issues. These should lead to innovative context-sensitive and intelligent adaptive assistance systems that support learning and training at the workplace.