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The purpose of this study is to explore teachers’ workplace informal professional learning and inform educational researchers, teacher educators, administrators and teachers about ways teachers learn to improve their practice. By questioning how teachers learn on-the-job to be better teachers and how school cultures position them as learners, this work generates hypotheses about relationships between the nature of workplace informal professional learning and its content and contexts. An ethnographic design based upon a grounded theory generates analytic categories from interviews and field notes through comparison of learning environments in three contrasting schools in two countries—Lithuania and the United States. Discourse analysis is employed to understand how teachers learned through interaction with students, colleagues, and administrators. The findings illuminate six facets of school culture that provide or fail to provide opportunities for informal teacher learning: architectural features of a school building; school mission statements; classroom environments; organizational arrangements; school traditions, and teachers’ professional relationships. The limitations of this study derive from its focus on school cultures as learning organizations that produces detailed thick descriptions, which are culturally specific and may not necessarily be transferable to other schools. The implications underline that teachers and teacher educators could enhance teachers’ professional learning by contributing to building and sustaining the opportunities necessary to maintain professional growth at teachers’ work places. The value of the study is in 1) defining specific cultural features in schools that create or fail to create opportunities for teachers to learn informally; 2) showing how teachers use these opportunities for their learning; 3) calling for re-evaluation of professional development systems to include informal learning as an important path for professional growth.