This study used two approaches to examine YouthLink as an example of a drop-in and case management model for working with youth experiencing homelessness. These approaches investigated the same group of 1,229 unaccompanied youth, ages 16 to 24 and overwhelmingly Black, who voluntarily visited or received services from YouthLink in 2011. Both approaches looked at the same metrics of success over the same time period, 2011 to 2016. One approach—Study Aim 1—examined the drop-in and case management model overall, asking whether YouthLink's service model resulted in better outcomes. It compared a YouthLink cohort with a group of highly similar youth who did not visit YouthLink but may have received similar services elsewhere. A second approach—Study Aim 2—investigated within the YouthLink cohort the ways in which YouthLink's drop-in and case-management approach worked toward achieving the desired outcomes.