Increasing global digitalization is changing the everyday language skills required to participate in society, to carry out professional activities, and to take advantage of educational opportunities. As a result, new linguistic and digital competences are required for migrants. At the same time, digitalization offers new potential for learner-oriented language learning. In this article, we compare the results of two studies on teachers of adult multilingual migrant learners. These teachers instruct learners at different levels of literacy and with varied prior formal learning experiences. Both studies are situated in the German education system. The results illustrate how teachers and learners can work together using digital technologies to promote language learning. We explore the opportunities for effective, multilingual, and motivating language learning, as well as the challenges faced by learners and teachers, pointing to the need for further training in digital technology for both groups.