This study explores the extent to which we can trust and rely on dogs to use technology in order to perform critical behaviors that enhance health, safety, and well-being. Through the use of such technologies, humans and dogs foster a more robust and supportive environment than either assistive technologies or canine assistants can provide alone. We implement a user-centered approach focused on natural observation, respondent field survey, scenario-based design prototyping, and ethnographic case studies, including interviews and photo journals as key methods. This approach presents opportunities for further advances in human-animal interaction, new strategies for advancing assistive technologies, and richer human computer interaction (HCI) experiences. These scenarios are increasingly inclusive of dogs as users of and contributors to more fulfilling interactions with technology.