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Middle school students’ readiness for successful online learning is essential, yet few reliable tools measure the critical skills they need to thrive in virtual environments. This pilot study validates the Middle School Readiness and Enrichment Survey (MSRES) instrument, explicitly developed to assess resilience, motivation, application confidence, study skills, writing proficiency, and peer support among middle school learners. Exploratory factor analysis with pilot data from 120 middle school students confirmed construct validity and internal reliability. Qualitative feedback from respondents reinforced construct validity and highlighted the instrument’s practical utility. The validated instrument offers educators and researchers an empirically robust tool for designing targeted interventions and promoting equitable, developmentally appropriate middle school level online learning experiences.