Researchers acknowledge the utility of external consultants in helping teachers address problem behavior. To build teachers' capacity, the author explored emerging roadblocks during a consultation process. This investigation involved consultation and training on multitiered positive behavior supports for early childhood co-teaching dyads who selected children with year-long problem behavior. Sessions were informed by teacher-child observations and teachers' data collection. Triangulated content analysis with peer debriefing and member checking suggested specific areas to address before participants could objectively engage in the assessment process. These obstacles included: difficulty defining concerns, focusing on variables outside their control (i.e., behavior's etiology, the role of parental caregivers), and establishing nonrevisited, early assumptions. This study provides a rare glimpse into roadblocks to behavior assessment in an early childhood setting. Implications are discussed, including the need for more proactive discourse in teacher preparation programs and in-service training to build educators' capacity to objectively assess prolonged problem behavior.