It has become increasingly difficult for the two major parties in Congress to reach agreement on major higher education legislation. As a result, the Higher Education Act is long overdue for reauthorization. Congressional stalemates on higher education legislation are not conducive to effective and productive governance in this important area of federal policy. The purpose of this comparative case study is to understand why some federal higher education legislative bills are successfully enacted while others, including some with bipartisan support, are not. Through the lens of negotiation theory, this study examines six federal higher education bills in order to understand the common characteristics of successfully enacted legislation and the common characteristics of unenacted legislation. Data sources include interviews with 28 policy actors and analysis of documents relevant to each case-study bill. Findings from this study illuminate factors that make the passage of federal higher education bills more likely, including leadership and presidential priorities, cost savings, noncontroversial issues involving sympathetic policy beneficiaries, urgency, favorable congressional rules, support from the higher education lobby, and avoidance of political victories for the opposing party. Understanding how and why Congress members reach agreements on legislation may help forge a pathway toward more effective legislating in the higher education policy arena.