A key assumption in past literature has been that human services workers become emotionally distant from their charges (such as clients or patients). Such distancing is said to protect workers from the emotionally draining aspects of the job but creates challenges to feeling and behaving compassionately. Because little is known about when and how compassion occurs under these circumstances, we conducted a multi-phased qualitative study of 119 correctional officers in the U.S. using interviews and observations. Officers’ accounts and our observations of their interactions with inmates included cruel, disciplinary, unemotional, and compassionate treatment. Such treatment varied by the situations that officers faced, and compassion was surprisingly common when inmates were misbehaving—challenging current understanding of the occurrence of compassion at work. Examining officers’ accounts more closely, we uncovered a novel way that we theorize human services workers can be compassionate, even under such difficult circumstances. We find that officers describe engaging in practices in which they (a) relate to others by leveling group-based differences between themselves and their charges and (b) engaged in self-protection by shielding themselves from the negative emotions triggered by their charges. We posit that the combined use of such practices offsets different emotional tensions in the work, rather than only providing emotional distance, and in doing so, can foster compassionate treatment under some of the most trying situations and organizational barriers to compassion.