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There is a lack of comprehensive research on Ecological Momentary Assessment (EMA) feasibility to study occupational stress, especially its long-term sustainability. EMA application in education contexts has also been sparse. This study investigated the feasibility of using EMA to study teacher stress over 2 years using both objective compliance data and a self-reported feasibility survey. It also examined the influence of individual and school factors on EMA feasibility. Participants were 202 sixth through eighth grade teachers from 22 urban middle schools in the southern United States. EMA was implemented via an iPod-based Teacher Stress Diary (TSD). Teachers recorded demands, stress responses, and resources during 12 days (6 waves) over 2 years. Feasibility was assessed via compliance data generated by the TSD (e.g., entry completion) and an EMA Feasibility Survey of self-reported user-friendliness and EMA interference. The results showed high compliance regarding entry and item completion, and completion time, which was sustained over time. User-friendliness was appraised as very high and EMA interference as low. Initial difficulties regarding timing and length of assessments were addressed via EMA method refinement, resulting in improved feasibility. Teachers’ ethnicity, age, marital status, grade/course taught, class size, class load, and daily workload impacted feasibility. The results supported the feasibility of using EMA to study work stress longitudinally and the value of continued feasibility monitoring. They also support EMA use to study teacher stress and inform EMA implementation in schools. Some teacher and school factors need to be taken into consideration when deciding on EMA implementation in education contexts.