This paper presents a perspective for looking at the development and implementation of large scale computerised HIS as a multi-level learning process. Drawing on the empirical evidences from the ongoing Health Information systems program ( HISP) initiatives on the development, customization and implementation of computerised HIS in Ethiopia, the paper analyses the learning mechanisms, learning outcomes and obstacles for learning at individual, group, and organizational levels. Empirical data on two distinct phases of software development and customization (District health Information Software (DHIS) versions 1.3 and 2.0) are contrasted. More specifically, we tried to show the dynamics of learning and the specific learning mechanisms by analysing and contrasting the interaction between IS developers and public health care domain experts, technological capacity at individual, group, and organizational levels, and organizational commitment and buy-in in the process of developing, customizing, and implementing the two distinct versions of DHIS software.