Homeless persons with dogs are often the subject of stigma, with the public criticising them for not having a proper lifestyle to care for a pet. There is solid documentation of how dogs enhance a homeless person’s life, but there are few publications that address the welfare of the dog. This descriptive study assesses the physical and behavioural health of dogs belonging to homeless persons through a One Welfare lens by observing animal/human well-being, environment, and “a life worth living”. A survey was carried out along with a visual assessment of the condition of the dog for 100 human-dog dyads in the Western United States. Results showed that dogs of homeless persons were well cared for and physically healthy (which was consistent with other studies), and had few behavioural problems, but did display evidence of separation distress while the owner was away. Results from this study can provide information that may lead to policy and practice changes, including, for example, changes to policies and practices prohibiting dogs from being kept with their owner while staying at a homeless shelter. Typically, shelters report that they do not have the resources to care for a person with a dog.