Outlines assimilation patterns by young adult immigrants using education, incarceration, and early childbearing as crucial “turning points” that determine the trajectory of their incorporation into American society. Historical information on immigration patterns, restructured educational demands in the workplace, and incarceration rates are examined to provide a perspective for the occupational situation faced by the current wave of immigrants from Latin America and Asia. Data from the 2000 Census and the Children of Immigrants Longitudinal Study (CILS) are utilized to outline education levels, rates of incarceration and early childbearing within ethnicity, gender and generation. The first of three major findings indicates a higher than average rate of incarceration among second-generation males, especially for those with low education levels, and illustrates the downward assimilation of a significant minority. Second, early and overall childbearing in second-generation women has decreased. Third, extremely high education levels of Asian immigrants and low incarceration rates have allowed this immigrant segment to follow a smoother assimilation path. Ultimately, the complex nature of the current immigration situation denies an easy solution; however, identifying the paths and mechanisms that lead to “virtuous instead of vicious” cycles can bring about positive results in this “new era of mass migration.”