The rapid development of digital technology and its pervasiveness in everyday life requires everybody to develop the skills necessary to engage with such technology for one's mundane tasks and communication needs. The first steps towards developing these skills can be particularly challenging for older adults, who might need to fundamentally adapt their learned and long-practiced routines. Maintaining motivation in these initial steps is crucial for sustained engagement. The present study examines factors that can contribute to promote motivation in a facilitated learning session based on Self-Determination-Theory. We conducted a longitudinal qualitative study in which we examined people's motivation to engage with digital technology, based on observational data as well as interviews with 33 older adults before and immediately after participating in a facilitated learning session. To investigate sustained effects on motivation, further interviews were conducted 3 months after participation. We found that satisfying the need for relatedness by learning together with peers and receiving support from facilitators was a prerequisite for this target group to develop a sense of competence and autonomy, which can lead to sustained motivation. Long-term motivational effects could not only be explained by the immediate effects of the learning intervention, but were identified to be dependent also on individual needs and predispositions. These findings were aggregated in a typology that identifies relevant influence factors and explains the potential motivational effects for different parts of the target group. It supports learning and technology designers to adapt to the addressed user group.