This study sought to investigate the factors affecting agents‟ liquidity challenges in Nairobi County. It adopted a mix method cross-sectional study of agents, master agents, provider representatives and bank representatives. The study had three-fold objective: to establish the relationship between agent factors and liquidity challenges, to establish the effect of supply side factors on agent liquidity challenges and to explore agent perceptions towards liquidity management mechanisms. Liquidity challenges were defined as too frequent or few rebalancing visits and high numbers of transactions denied due to lack of float. The study found that agents experience in the agency was an important determinant of the frequency of rebalancing because they have established rebalance routines and relationships with rebalancing facilitators thus minimizes liquidity outages. In cases where rebalancing is conducted by owners, there are more rebalancing visits due to the instantaneous decision making as compared to when employees perform rebalancing due to longer decision making approval processes which leads to prolonged liquidity outages. The capital layout of the main business is another important determinant of the frequency of rebalancing visits. Higher capital investments in their primary business means less liquidity outages as the agency can tap into the working capital flows of the primary business to meet its liquidity needs. Banks were the primary mode of rebalancing to acquire electronic float. Distance to the nearest bank branch was a very important factor in determining liquidity challenges whereby agents located further away from banks denied more transactions due to lack float and rebalance less often than agents located closer to banks. This was attributed to the travel costs incurred during rebalancing visits and the opportunity cost such as loss of potential business of the primary business. The study recommended continuous revision of the profile of a suitable agent to include experienced, owner-operated and high cash-flows of the primary business. The study also recommends an industry rather than provider specific perspective to solving liquidity challenges. Managerial level recommendations included decentralization of liquidity hubs beyond bank branches, regular agent training and monitoring.