(1) Background: COVID-19 may deteriorate some aspects among individuals with attention deficit hyperactivity disorder (ADHD). Although some positive aspects were reported during the pandemic, it remains unclear how COVID-19 qualitatively influences their living context; (2) Methods: this study employed interviews with four participants with ADHD during the declaration of emergency issued in Japan. The study was a part of ongoing coaching as a psychosocial intervention for ADHD, which was initiated long before the pandemic. The data were the answers to the question: “how are things going with participants during this pandemic?”. In a qualitative analysis, the researchers coded the data to identify different themes and sub-themes; (3) Results and Discussion: the qualitative data analysis yielded five themes: (1) Terrible feeling caused by frustration, stress, and anger; (2) Closeness due to the internal difficulties and conflict; (3) Deteriorating ADHD symptoms and executive function related matters; (4) Condition is the same as usual; and (5) Positive aspects associated with the self-lockdown. As a whole, these results show that the COVID-19 pandemic could be a factor in inducing psychological distress in the participants who adjust relatively better at work/school but did not do well at home before the pandemic; (4) Conclusions: this study indicates the need for special support for individuals with ADHD, especially those who originally had difficulties at home.