There is limited use of empirically supported mental health interventions in schools. Leveraging technology may reduce some barriers, however, use may still be limited. To further understand variable intervention use, this study investigated the challenges experienced by teachers invited to implement a daily report card (DRC) intervention aided by an interactive website called the DRC.Online (DRC.O). The DRC is a structured approach to the delivery of a tailored positive reinforcement intervention to support individual students struggling with attention and/or behavior difficulties delivered by teachers with daily feedback to the student themselves and their caregivers. The study was embedded within a pilot rollout of the DRC.O in elementary schools in two school districts in Canada. Data for this qualitative inquiry were derived from 21 semi-structured interviews and two focus groups conducted with teachers and other school personnel who had varying levels of DRC.O use. A descriptive qualitative approach was used. Five constructs were identified: (1) "Intervention Demands for the Teacher," (2) "Finding and Creating a Fit for the Intervention," (3) "Perceived Focus on the Negatives," (4) "Managing Technological Components," and (5) "Influencing Contextual Factors." Each construct contains aspects of challenges that may have influenced the extent of use of the DRC.O. Some of the identified factors overlap with challenges identified in previous studies of intervention implementation; however, details within the above constructs identify additional nuances that may inform specific adjustments that may improve uptake and implementation.