Recent literature has documented the negative intergenerational effects of parental incarceration on educational outcomes. Of increasing concern are the ways in which the stigmatic labeling and social exclusion of once incarcerated parents can create negative outcomes in the educational success of future generations. Not fully answered in the literature is why the experience of parental incarceration generates these negative effects. Using multigenerational data of parents linked to adolescents in the Houston School District (N= 1,297), this study analyzes three possible explanations of the reduced educational performance of those experiencing parental incarceration: individual, group, and/or structural level factors. Using multilevel linear and logistic regression models, this study finds that those experiencing parental incarceration do not adopt individual attitudes of educational rejection and low aspirations, but instead develop closer ties with potentially delinquent friends (i.e., group level factors) and are more likely to experience structural neighborhood disadvantage (i.e., structural level factors) than their counterparts who have not experienced parental incarceration. These findings are discussed in light of a racialized history of mass incarceration.This research study also uses 20 in-depth interviews with adult respondents in Central California who experienced parental incarceration at some point in their life. This study reveals that there are many long-term effects of incarceration on families and that those who experience parental incarceration often experience demobilization through: transference of stigma, emotional and financial strain, and severe residential instability and familial restructuring. These elements combine to produce negative consequences for family members who often have never been convicted of crimes themselves. The increased deprivation of resources and transference of stigmatization to the second generation can demobilize whole segments of the population. This dissertation also reveals that parental incarceration is more secretive and deceptive than other forms of separation, and this is mostly due to the stigma around the incarceration. This paper utilizes qualitative data in California, and discusses instances when parental incarceration is shrouded in secrecy, and cases when children grow up and “Google” why the parent is gone. Sometimes they were shocked at what they found, sometimes they were reunited with their parent, and sometimes they came up empty. The findings of this research article suggest that mechanisms of parental incarceration operate differently from other forms of separation. The secrecy and deception experienced by those losing a parent may have negative emotional consequences later on in life.