The transition from student to occupational therapy practitioner is challenging. In South Africa, this transition is undertaken in rural and underserved areas, as graduate health professionals are deployed by the government for a year of compulsory Community Service. This study set out to establish the characteristics of these practice settings, the resources available for occupational therapy services, the availability and quality of supervision, and participants' perceived ability to communicate with their patients and negotiate cultural differences. A cross-sectional survey design was utilised and a questionnaire was sent to all occupational therapists completing Community Service in 2013 (N = 240). Data were analysed using Stata 12 and IBM SPSS Statistics 21.0. Frequencies and percentages were calculated for categorical variables and associations tested with Odds Ratios and the Pearson's Chi square test. Responses to open-ended questions were post-coded. A 44.3% (n = 103) response rate was achieved. Practice settings often provided few resources. Although most participants had supervisors (89.6%), many did not find supervision satisfactory (65.9%). Communication difficulties featured strongly (73.9%), but the majority of participants felt they possessed basic cultural competence. Participants worked within complex practice settings that were frequently resource-restricted with less than satisfactory supervision. Practice required cultural competence and an ability to work across language barriers. Undergraduate curricula need to be tailored to equip new graduates to navigate these contextual realities. Furthermore, human resourcing strategies need to be evaluated and effective supervision and support structures need to be developed. © 2019 Occupational Therapy Australia.