Massachusetts was one of the first states to receive an implementation grant under the federal School-to-Work Opportunities Act. The authors explore the state's STW programs before, during, and since the period covered by the grant, highlighting local variations and the challenges posed by the shift of reform efforts toward standards and accountability. IN MASSACHUSETTS, the advent of school-to-work (STW) was met with great hope. At its most expansive, it was envisioned as a systemic effort that could reach all students by addressing a mix of skills -- academic and work-related -- that they would need for future success. As such, STW was seen by its proponents as a potential vehicle both for achieving education reform and for strengthening the preparation of the work force. Massachusetts in the early 1990s did, indeed, appear to be fertile ground for STW. Early programs had been developed and piloted here, and a good amount of the national thinking and research on school-to-work strategies had some kind of Massachusetts connection. A comprehensive education reform act that included elements consistent with STW was in the making. But in Massachusetts, as elsewhere, there were notable challenges to overcome if the broad STW vision was to be realized. Federal STW money was modest venture capital, and it would always be dwarfed by funding from other sources. And, at the outset, STW was considered by many within the education sector to be a narrowly focused effort, appropriate only for students who sought direct entry into the labor force following high school. Now that the federal School-to-Work Opportunities Act (STWOA) has sunsetted, what remains in Massachusetts of this potentially powerful initiative? And to what degree did STW really become an integral part of the overall school reform agenda? We believe that three elements needed to be in place for STW to be established as a central piece of school reform: 1) state policy and funding that supported STW activities, 2) an early and strong commitment to STW by local leadership, and 3) empowered local intermediary organizations that could pull schools and community partners together and could provide the staff capable of designing, launching, and expanding programs. So what happened? The experience in Massachusetts was mixed. From a state policy perspective, there were some major initiatives that helped develop STW and that still sustain significant levels of STW programming today. At the same time, there were shifts in the emphasis of state education policy that made it difficult to adopt STW as a key reform strategy at the local level. Still, some districts did embrace STW as a central piece of their reform efforts. But in most, a weak commitment and a shortage of staff meant that STW -- a challenge to implement anywhere -- typically remained at the margin and did not become the driving force behind broad changes in educational delivery that its proponents had hoped for. Fertile Ground The beginning of the school-to-work effort in Massachusetts can be traced perhaps as far back as the establishment of the Boston Compact in 1982. This was a historic agreement between leaders of Boston's business community and the school district. It established expectations for school improvement, coupled with employer pledges to provide part- time and summer job opportunities as well as priority hiring for Boston public school students and graduates. Implementation of the Compact's employment goals became a core function of Boston's Private Industry Council (PIC). Over time, the PIC and the Compact focused on creating internship experiences for young people, an effort that led to the nationally recognized ProTech model and had a significant influence on the design of programs funded by the STWOA. Meanwhile, by the early 1990s, education and business leaders throughout Massachusetts recognized the need to substantially reform public education -- both to improve academic outcomes for youths and to support the state's economic competitiveness. …