Although criminal records in the United States are more publicly accessible than ever before, we lack knowledge about how record‐bearers seek to overcome the negative consequences associated with a visible criminal record as they apply for jobs, housing, and financial aid. Furthermore, although criminal histories record all arrests—and not just those that result in conviction—researchers have yet to compare how those with more extensive versus minor criminal records cope with criminal record stigma. We present interview data from a comparative study of expungement‐seekers (N = 53) who have petitioned the courts to remove their criminal records from public view. One group had extensive criminal records (46 percent); the other group had more minor criminal records (54 percent). Several key findings emerged. First, both groups of participants tried, but failed, to persuade potential employers and landlords to overlook the criminal record. They also faced restricted educational opportunity. Second, participants in both groups expressed distress that criminal justice contact could follow them throughout their lives, subjecting them to ongoing stigma. However, those with extensive versus minor criminal records offered different rationales explaining why the visible criminal record history unfairly burdened them. Implications for reintegration theory and policy are discussed.