The purpose of this study was to explore first time handlers’ experiences when working with an assistance dog (AD). Interviewees included seven first time AD handlers and 14 other individuals close to these handlers, including family members, carers and AD instructors. Semi-structured interviews were conducted six months and one year after each handler received their AD. Interview questions were informed by the Thriving Through Relationships theory of social support and previous interviews with the participants. Inductive content analysis corroborated previous findings regarding the benefits that ADs provide. In addition, four factors were revealed to substantially influence the challenges handlers experienced when learning to utilize their dog. These included the handlers’ medical conditions, cognitive ability and social environment, and dog-related factors. Organizations would benefit from considering these factors in their operational processes.