The present paper takes the approach of critical hermeneutics in human rights education (HRE) that has been developed theoretically and tries to operationalize it in pedagogical practice. In particular, a group of Greek-Cypriot teachers were trained in a series of workshops on how critical hermeneutical approach (CHA) could be taught in the context of HRE. The paper explores teachers' difficulties with and perspectives of CHA during the training designed and offered by the authors. The findings show how, in addition to epistemological issues involved concerning the meaning and implications of the CHA, the particularities of the local context (ethnic conflict, pedagogic traditions, educational structures) influenced the uptake of this approach. The implications are discussed in relation to the need to identify the difficulties teachers have with specific pedagogical approaches of HRE as they become manifest contextually, and the need to design teacher training in which teachers have opportunities to reflect upon and engage with these difficulties through a critical interpretive lens.