This evaluation of the second-year (1986-87) implementation of the middle school Dropout Prevention Program (DPP) of the New York City (New York) Dropout Prevention Initiative (DPI) focuses on student characteristics, program services, and outcomes. The 29 DPP middle schools were divided into two models. Fifteen of the schools comprise Project Connect, with services provided by the New York City Board of Education (BOE); the other 14 were served primarily by community-based organizations (the CBO model). Data were analyzed from the following sources: (1) the Board of Education's student data base; (2) one-time check-off lists of services provided; (3) a monthly summary of service reports; and (4) a survey of 1,718 targeted students. Summary findings included the following: (1) implementation had reached a routine stage of activity for most DPP components in most schools by June 1987; (2) there were very large differences among schools in the targeted students' levels of risk; (3) the frequencies of services were comparable between the CBO model schools and the Project Connect model schools, with the exception that the CBO schools emphasized individual and group counseling more than the Project Connect schools; (4) overall, the program failed to improve students' chances of completing high school; (5) those schools that showed significant gains were characterized by initiative and creative use of resources. Recommendations for the third year of the program are included. Statistical data are included on 32 tables and 26 graphs. (FMW)