Academic advising plays a critical role in student engagement and persistence at community colleges, and colleges are increasingly adopting advising technologies to increase their capacity to support students. However, much remains unknown about the process of planning for and implementing technology-mediated advising redesigns. To explore these reforms' complex dynamics, we adapted Urie Bronfenbrenner's ecological systems theory of human development, conceiving of the student advising experience as embedded in three interrelated contexts: the external environment (the political, economic, and cultural environment outside the institution), the institutional environment (where changes in practice are implemented), and the interpersonal environment (where advising interactions occur). Using interview data collected from a diverse group of stakeholders at two community colleges and two broad-access four-year institutions, we identified several dynamics that have implications for practitioners, funders, and policymakers looking to enact technology-mediated advising reforms. External dynamics included involvement in national college completion organizations and initiatives, state policies related to college completion, and state and local economic conditions. Institutional dynamics included resource constraints, the degree to which advising policies and procedures were centralized, and approaches to managing institutional change. Finally, interpersonal dynamics included individual advising approaches, advising capacity, and reactions to technology.