In the past thirty years educational attainments in the United States have stagnated, particularly for low-income Americans. As a result, income-related gaps in educational attainments have grown. These gaps are important because education has historically been the key mechanism for intergenerational socio-economic mobility in the U.S. While the research and policy community has spent a great deal of energy documenting and exploring the important issue of racial gaps in education, less attention has been paid to income-related gaps. Recent evidence suggests that while racial achievement gaps have narrowed over the past few decades, income-related achievement gaps have grown substantially (Reardon, 2011). In this analysis, the researchers use dataset from Massachusetts to document income-based gaps in educational attainments and marshal evidence to examine the role of schooling and school-related policies in accounting for them. In most of the analyses the focus is on students who were first-time 8th graders in 2002-03 and 2003-04 school years. The results suggest several important lessons for educators and policymakers: (1) income-related gaps are large and important. They reflect differences in skills and behaviors that emerge early in students' educational careers, often even before they enter the public school system. Early intervention to remediate these gaps is critical; (2) income-related gaps in both academic achievement and educational attainments are smaller for students who have been in school in the state longer suggesting that the system is having some success in closing these gaps; and (3) while early gaps exist, they do not tell the whole story and even high school does not appear to be too late for intervention. Something appears to be happening to low-income students in high school that makes them fall out of the educational pipeline. Even among demographically similar students who persist to 10th grade, have similar test scores, and say that they plan to attend college, low-income students drop out of the pipeline at much greater rates than their higher-income peers. Five figures and three tables are appended.