In 1992 and 1995, data were collected from 29 Navajo, reservation-residing teenage mothers. In 2007, follow-up data from 69% (n = 20) of the original sample were collected. Intensive interviews, grounded in ecological systems theory (U. Bronfenbrenner, 1989), allowed for contextual examination of the women's developmental trajectories. Significant educational accomplishments and a strong work ethic (i.e., individual level) exemplified the majority of respondents. Relationships with families of origin and intimate partners (i.e., microsystems) and connections between these (i.e., mesosystems) promoted and challenged participants' optimal development and were significantly influenced by macrosystem factors (e.g., economic constraints, physical isolation). Implications for service provision and continued research are discussed. (Contains 1 table.)