Circles of Support and Accountability (CoSA) are comprised of approximately five trained Circle volunteers who provide support during reentry to one core member previously convicted of a sexual offense. In 2008, the Minnesota Department of Corrections implemented the Minnesota Circles of Support and Accountability (MnCoSA). In-depth interviews were conducted with 33 MnCoSA volunteers and 10 core members to gain an understanding of (a) what makes volunteers desirable to core members, as well as (b) what makes CoSA desirable to volunteers. The study finds core members express a desire for the availability and consistency of volunteers, a preference for certain types of volunteers, and consistent with volunteers’ perceptions, a belief that CoSAs offer particular benefits for volunteers. Implications for recruitment of volunteers and optimal structuring of CoSAs are discussed.