In 2018, a multisite case study investigated the agricultural challenges faced by Maldivian farmers and farming stakeholders. The study interviewed a total of 373 farmers and stakeholders from 51 islands across 15 atolls. In their own words, farmers and stakeholders identified factors in macro and micro levels agricultural systems that are related to poor connectivity between farmers and the markets. This research article conducts a deeper investigation into these factors using the Ecological Systems Theory. In this investigation, the data clearly reveal that any efforts towards market connectivity resolution must address the individual within the context of the greater, extrinsic challenges present in the interrelated systems of farming in the Maldives. While the individual is placed at the smallest level of a greater system, and the interconnections of the larger systems are great in impact, the individual is ultimately the decision maker on what and how things work, and how effective they will be. In this article, five recommendations are identified to enhance farmers’ connectivity to markets. This first-person perspective of smallholder farmers is an essential contribution to understanding what measures are needed to address connectivity challenges between Maldivian farmers and the markets they would like to supply.