Concerned about the persistently high dropout rates from big-city secondary schools, education leaders are trying a new approach to increasing the graduation rate--multiple pathways to graduation. Multiple pathways initiatives are relatively new and far from proven. Even the most advanced examples face significant issues, i.e., the need to demonstrate that students who graduate via multiple pathways are as well prepared as graduates from regular high schools. However, multiple pathways initiatives are clearly a significant new development, using analysis of student data to provide much better targeted remedies to students' individual problems than were possible in earlier dropout prevention programs. This report is based on interviews with district and foundation leaders and scholars who were among the originators of the multiple pathways idea. This report provides snapshots of different approaches to multiple pathways evident in New York, Portland, Oregon, other Eastern and Midwestern cities, and a California multi-district collaborative. This report distinguishes three different approaches to providing multiple pathways to graduation: (1) Targeted Population approach; (2) District-Wide approach; and (3) Linked Learning approach. This report describes these approaches in detail, provides examples of each, and analyzes what district leaders must do if they want to implement one or another of the approaches. The report ends with an analysis of how well the different multiple pathways approaches are likely to work in districts with particular characteristics. Appendices include: (1) Interview Questions; (2) Interviewees; (3) Graduation Rate Measurements; and (4) Suggested Effectiveness Dashboard. (Contains 1 figure and 23 footnotes.) [This paper was written with Paul Hill.].