Children born to teen mothers may experience less responsive and supportive parenting and are at heightened risk for a range of social, developmental, and health issues. There is literature to support the positive impact of grandmothers on teen parents and their children. However, what if the teen’s mother is also limited in her parenting capacities? How do parenting capacities across these two generations of mothers affect the developing child? In this ongoing study we are examining two important aspects of parenting capacities, attachment quality and executive functioning, in teen mothers (TM) and their biological, co- residing mothers or grandmothers (GM or GGM). Both are essential components of effective parenting, but little is known about their impact on young children’s development when raised by two generations of parents. In a cross- sectional, descriptive design, a convenience sample of 50 TM/GM dyads with children 1 to 3 years old is being recruited from two urban teen-tot clinics. Participants complete a paper-and-pencil measure of attachment quality and a computerized measure of multiple aspects of executive function (working memory, inhibitory control, cognitive flexibility). A standardized maternal report measure is used to assess child developmental status. The biggest challenges of the study thus far include recruitment and transience of the study population. Progress to date and experiences from recruitment and data collection are discussed, as well as successful strategies to address challenges.