The spring phase of the pandemic made the education of adolescents with specific learning difficulties (SpLD) challenging. In the present study, which included 122 adolescents with SpLD (50% from Slovenia, 50% from Germany), we investigated how Slovenian and German adolescents with SpLD perceived and solved some of the challenges of distance learning. The study data were collected with two online questionnaires (in Slovenian and German, respectively). Slovenian adolescents were statistically significantly more likely than German adolescents to mention problems with attention, the importance of multisensory learning, and the importance of being able to choose the time to learn, as well as psychosomatic problems. Slovenian adolescents had more experiences with praise from teachers during the pandemic and they also mentioned more issues with the transition to distance learning and the use of information and communication technology. Younger adolescents had more parental help. Male adolescents were more likely to report that they did not have the right spatial conditions for learning. German adolescents spent more time chatting on social media and experienced less support for learning. Female adolescents were more likely to express fear of the pandemic and a lack of learning support, while male adolescents across the sample missed their peers more. Most of the respondents came from families in which the pandemic did not cause serious material and spatial problems, but German adolescents were statistically significantly less likely to feel these consequences. According to the respondents, the spatial and material conditions were similar in both countries.