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Although much research has focused on the process of immigrant incorporation, some significant components of this process remain undertheorized: time of arrival, local context, legal status, and racialization. This paper compares 60 young adult Mexicans’ experiences in suburban Pennsylvania and New York City as influenced by these factors. Half of the thirty Pennsylvania respondents arrived during or before the 1980s. Most respondents and their families arrived in New York after 1988. This timing is significant since seventeen Pennsylvania and eleven New York respondents were born in Mexico. Given the provisions of the 1986 Immigration Control and Reform Act, and that most Pennsylvania respondents’ families were recruited for agricultural labor, all respondents born in Mexico attained status. New York respondents’ families, however, arrived too late to qualify for citizenship under IRCA, so those born in Mexico remained undocumented; seven others born in the New York had to negotiate their parents’ illegality. Consequently, incorporation in Pennsylvania occurs in relation to and is constrained by middleclass whiteness, where, although respondents achieve structural incorporation in being able to attend and graduate from a well-renown college, they are still perceived as not belonging. Pennsylvania students experienced racialization and social exclusion through interpersonal interactions with white middleclass peers and school officials that marked them as foreign and inferior. In New York, students experience incorporation while contending with the larger inequalities of living and going to school in lower-class Black, Latinx, and immigrant communities. Although undocumented status further complicates respondents’ ability to consider and afford college, existing legislation, not present in Pennsylvania, allow undocumented students some structural incorporation in being able to enter, finance, and complete college. Still, all New York students experienced racialization—through discourses in politics, media, and workplaces that rendered them “illegal” and criminal—as social incorporation.