Section one is a systematic literature review that has carefully explored the inferred relationship between adult attachment style and empathy, with consideration to the theoretical underpinnings to such a relationship. The papers reviewed were quality appraised and methodological weaknesses were acknowledged throughout. The review suggests that there may be a positive relationship between attachment security and empathic traits. This is followed with a discussion highlighting some of the associated clinical implications, particularly with respect to professions who have a caring or supportive role towards people in need. Section two addresses some of the issues raised in section one, by going on to explore the influences of attachment style and empathy in a scarcely researched area: probation. The study makes use of an online survey with a total of 145 probation officers participating. Social distance is considered in relation to offence type, officer characteristics and potential study confounders. The clinical implications are discussed and recommendations made for future research. Finally, section three critically appraises the above empirical research. This includes further thoughts regarding the ramifications of the findings, considered in the context of probation services at the time, including political and societal influences. Personal reflections are made with regard to conducting this research taking the above into consideration, and ideas for alternative ways to conduct similarly beneficial research are presented.