The 1996 federal welfare-to-work legislation generated significant debate regarding what role public transportation should play in facilitating lower welfare rates. Given this debate, transportation has been called the “to” component of welfare-to-work. In this paper, we present findings from three case studies that examine job accessibility and reverse commute transportation programs in the Chicago, Kansas City, and San Francisco metropolitan regions. We explored how institutional and/or grassroots support prevented or fostered the innovation and implementation of non-traditional Access-to-Jobs and Reverse Commute (JARC) programs. Our findings suggest that institutional support and grassroots support are necessary ingredients for the implementation of innovative transportation programs for low-income families.