Canine hypoadrenocorticism is a rare chronic disease, which demands intense dog-owner interaction, as its treatment requires to be individualised. The aim of this study was a qualitative analysis of the challenges owners face when dealing with the disease, especially regarding its management and how this affects quality of life. By promoting an online discussion between owners, we transcribed and summarised their experiential knowledge in dealing with the disease. Owners were recruited for the online seminars via social media. After a theoretical introduction, participants were free to share experiences and ask questions. The recorded events were retrospectively analysed. Twenty-four owners of 22 Addisonian dogs took part in four events. Owners felt most “traumatised” when experiencing their dog’s acute adrenal crisis. The initial adjustment phase and distinguishing the non-specific symptoms of hypoadrenocorticism from those of other diseases were also challenging. Overall, owners were well informed on the disease and committed to its long-term adjustment. Adrenal crisis and the initial adjustment phase may be more burdening to owners than expected. Understanding what their clients’ concerns are, can help veterinarians provide better care and reduce the negative impacts of canine hypoadrenocorticism. Promoting peer to peer support, as well as providing a framework for participative communication might also help.