Although the general field of education has numerous studies that document the challenges of urban schooling, we still know relatively little about the unique features of urban physical education. Moreover, we have virtually no studies that specifically examine the challenges of the urban context from physical educators' own perspectives. Therefore, this study used situated learning theory to examine the challenges that urban physical educators believe they face that significantly shape their development as teachers. The study took place in a large urban school district in the Midwestern U.S. with 46 elementary physical education teachers. Twenty-four were male and 22 were female; 26 of the teachers were African American, 19 were Caucasian, and 1 woman was Hispanic. The teachers ranged in experience from 1-37 years (M=17.87). At the time, the school district educated approximately 166,000 students, 91% were African American and 5% were Hispanic. Over 70% of the students qualified for free and reduced lunches and the city was routinely rated in the top five most violent urban centers in the U.S. Data were collected through semi-structured interviews, followed an interview guide, and were audio-recorded and later transcribed. Teachers were interviewed individually (1-5 times) and in small groups (2 times) across one school year. Data were analyzed using analytic induction and trustworthiness strategies included member checks, peer debriefing, and a researcher journal. Data analysis revealed five significant challenges that these urban physical educators faced in their teaching contexts that influenced their thinking and teaching. These challenges included coping with insufficient instructional resources, the need for culturally relevant instruction, combating the influence of community violence in the classroom, the need for games in urban physical education, and teaching in a “culture of basketball.” Each theme discusses ways that these teachers believed the challenges influenced their thinking and teaching, strategies they have employed over the years to overcome the challenges, and the outcomes of those strategies on the teaching environment and student learning. The discussion centers on interpreting these teachers' perspectives through the lens of situated learning, connecting their perspectives to broader urban education literature, drawing implications for teacher education and professional development, and offering directions for future research into the life and work of urban physical educators. Keyword(s): multiculturalism/cultural diversity, professional development, research