Stakeholder involvement is often a legally required activity for transit agencies. Optimally this process begins at the earliest stages of any given project and involves two-way communication and interaction that can be reflected in the resulting plans or project designs. Despite federal statutes and regulations mandating meaningful public input for federal capital funding consideration, approaches to fulfill these mandates successfully remain difficult, and stakeholder involvement practices often fail to have a deep impact on planning outcomes. A gap often exists between implementation plans and the satisfaction of stakeholders. Guided by prior research and applying cognitive mapping methods, this study uses a rail line reconstruction project of the Chicago Transit Authority in Illinois as a case study to systematically understand the gap in expectations and interpretations of success among stakeholders. Findings identify four important categories of goal nonalignment that act as barriers to optimal interaction that can lead to mistrust. Conclusions identify potential solutions for bridging the gaps.