Many attempt to address the documented achievement gap between urban and suburban students by offering special programs to enrich urban students' academic experiences and proficiencies. Such was the case in the study described by DeGennaro and Brown in which urban students participated in an after-school technology course intended to address the "digital divide" by giving these youth supported experiences as technology users. However, also like the initial situation described in this study, instructional design that does not capitalize on what we know about urban education or informal learning contexts can actually further damage urban youths' identities as learners by positioning them as powerless and passive recipients instead of meaningful contributors to their own learning. The analysis presented in this forum is intended to further the conversation begun by DeGennaro and Brown by explicitly complexifying our consideration of context (activity structures and setting) so as to support the development of contexts that afford rich learning potential for both the urban students and their learning facilitators, positioned in the role of teachers. Carefully constructed contexts can afford participants as learners (urban students "and" teachers) opportunities to access rich identity resources (not typically available in traditional school contexts) including, but not limited to, the opportunity to exercise agency that allows participants to reorganize their learning context and enacted culture as needed.