In the U.S. Congress, the House Committee on Rules (also referred to as the “Rules Committee”) has become one of the most exclusive congressional appointments for members to receive. This committee’s ability to shape the legislative pathways for bills before they reach the House floor for votes is arguably its most important role. There are four types of special rules that the Rules Committee assigns: open, modified-open, structured, and closed. The most restrictive types of special rules are structured and closed rules—jointly referred to as restrictive special rules. Restrictive special rules often limit the scope and number of amendments for bills, and the amount of time for floor debate. Since the mid-1990s, the Rules Committee has increasingly used restrictive special rules. For example, four times the number of closed rules were assigned in the 115th Congress (2017-2019) than in the 103rd Congress (1995-1997)—with both Congresses having similar amounts of special rules overall. Even amidst this noticeable trend, few empirical studies use bill-level analyses to assess which bills are more likely to receive restrictive special rules. This dissertation uses an original Special Rules Bills Dataset and Craig Volden’s and Alan Wiseman’s Legislative Effectiveness Dataset to examine the relationship between special rules and bill-level characteristics (e.g., bill issue areas, political ideology, bill sponsors/co-sponsors, and bill fate). Furthermore, this dissertation provides new insight on rising restrictive special rule assignments in the 107th (2001-2003), 110th-116th (2007-2021) Congresses and reports four main findings. First, results show that the Rules Committee is more likely to assign restrictive special rules to bills with majority party sponsors and to bills with fewer out-party cosponsors. Secondly, although appropriations bills often receive special rules, they are more likely to receive open/modified-open rules. Third, subcommittee chairmen are more likely to sponsor special rules bills. Finally, results show that restrictive special rules are more beneficial to bills addressing social welfare or civil rights than they are to bills addressing defense or public lands.