This article examines the establishment and publication of green plans and green public procurement (GPP) policies in Japanese municipalities. The purpose of the study was to investigate these green policymaking initiatives from a contingency theory perspective. The first research question examined contextual factors for green policymaking. The second research question focused on barriers and enablers. For RQ1, through hypothesis testing and a regression analysis (n = 1663), we found that green policymaking differs by organization location, organization size, and organizational green capabilities. More specifically, we identified prefectures where municipalities score relatively higher as well as lower. Second, we found that larger (vs. smaller) municipalities undertake more (vs. less) green policymaking initiatives. Third, we observed that organizations with more (vs. less) green capabilities develop more (vs. less) green initiatives. For RQ2, through a descriptive and cluster analysis, we identified dominant barriers and enablers to establishing a GPP policy. The dominant barriers include a lack of information, lack of staff, and cost concerns, whereas manuals and example forms are important enablers. These findings are highly relevant to understanding and supporting green policymaking in Japanese municipalities.