Abstract: Mentoring is recognised as an effective learning method in the transition from higher education to working life. Digitization of education brings new challenges to mentoring competencies and mentoring implementation methods. This paper examines how the initial stage of an eMentoring training developed by three Finnish universities of applied sciences is delivered to meet the authentic learning principles (Herrington et. al., 2010) of the digital age. Authentic tasks emerged as the strongest authentic learning elements, while the weakest element was collaborative construction of knowledge. This is a critical development challenge as collaborative learning can be seen as specific affordances of this educational model. Development of the eMentoring training needs to focus on increasing learner-centeredness applying e.g. the Flipped learning model and utilizing more effectively sharing of expertise in learner groups. A balanced design of authentic learning must be ensured in the training.