Adaptive K-12 mathematics platforms often show low sustained student use, a pattern termed the 5% problem. Although prior work has developed analytics and interventions to identify disengagement, less is known about how teachers make sense of persistence challenges in individualized learning classrooms. This study reports on a 90-minute participatory design workshop with 12 U.S. middle school mathematics teachers who use i-Ready Math weekly. Teachers generated needs through open-ended prompts, card sorting, and collective voting. Thematic analysis identified four recurring dimensions of low persistence spanning motivation and buy-in, cognitive roadblocks, resilience under challenge, and contextual barriers. Teachers emphasized the need to identify where students become stuck and recognize silent disengagement, prioritizing support for diagnosis and timely instructional response over aggregate usage metrics. These findings reframe the 5% problem as a situated instructional challenge and suggest a need for teacher-facing systems that support interpretation of student persistence through both cognitive and contextual evidence.

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