People with experience of homelessness commonly suffer from poor oral health and are likely to have low-level engagement with dental services. 'Teeth Matter' was a pilot study developed to examine whether peer education could result in improved plaque management among people who are experiencing homelessness. Based on the experience gained from developing and implementing the study, and taking into consideration the views of everyone involved, this paper provides a list of suggestions and resources that can be used to improve engagement of this population with oral health promotion activities. Some of the learning points are also applicable in the clinical setting.