Increasing attention is being given to the challenging of racism and racial harassment in health care organisations. Very little, however, is known about anti-discriminatory practice in the health services, or how professionals give meaning to ‘race’ in their work with service users. This paper examines these issues through representations of the ‘dilemmas’ that were talked about by hospice staff in managing incidents of racial harassment amongst service users. By addressing the micro-interactional dynamics of this work, specific attention is given to representations of the cognitive and emotional dimensions of anti-discriminatory practice: that is, how professionals talk about how they think and feel in working with, and sometimes attempting to challenge, racist service users. The paper suggests that the recognition and exploration of staff dilemmas in dealing with racism has much to contribute to the analysis of professional roles, values and expectations, while also having implications for policy and service development.