Despite a wide recognition of the importance of learning capacity and diversification, enabling and constraining factors, and external assistance in facilitating long-term livelihood recovery (LTLR), there is a paucity of comparison for a nuanced understanding of interconnections among the three themes (learning capacity and diversification, enabling and constraining factors, and external assistance) in different societal and disaster scenarios. Accordingly, this article employs a cross-national comparative approach in examining the interplay of these three factors in LTLR, within rural communities, following the two international post-disaster case studies, the 2007 Cyclone Sidr, Barguna, Bangladesh and the 2008 Wenchuan earthquake, Sichuan, China. This cross-national comparison indicates that the affected communities in both cases experienced extreme challenges in LTLR while illustrating the differences. Learning capacity and diversification facilitated asset loss recovery and risk mitigation in the Sidr case, while the Wenchuan case demonstrated a limited learning opportunity for livelihood diversification. Enabling and constraining factors were identified in both case studies. Particularly, people-place connections positively shaped the LTLR in the Wenchuan case while producing negative results in the Sidr case. External assistance facilitated livelihood provisioning, protection, and promotion for the Sidr case; in contrast, giving little, if any, credence to the local traditional livelihood practice, the top-down external interventions in the Wenchuan case jeopardized the rural communities LTLR. This article defends that promoting grassroots participation in community reconstruction and recovery and strengthening grassroots livelihood learning and practice capacities would advance LTLR.