Information Systems (IS’s) have provided organisations with huge efficiency gains and benefits over the years; however an outstanding problem that is yet to be successfully tackled is that of the troublesome maintenance phase. Consuming vast resources and thwarting business progression in a competitive global market place, system maintenance has been recognised as one of the key areas where IS is failing organisations. Organisations are too often faced with the dilemma of either replacement or the continual upkeep of an unwieldy system. The ability for IS’s to be able to adapt to exogenous influences is even more acute today than at any time in the past. This is due to IS’s namely, Web Information Systems (WIS’s) increasingly and continually having to accommodate the needs of organisations to interconnect with a plethora of additional systems as well as supporting evolving business models. The richness of the interconnectivity, functionalities and services WIS’s now offer are shaping social, cultural and economic behaviour on a truly global scale, making the maintenance of such systems and evermore pertinent issue. The growth and proliferation of WIS’s shows no sign of abating which leads to the conclusion that what some have termed as the ‘maintenance iceberg’ should not be ignored. The quandary that commercial organisations face is typically driven by two key aspects; firstly, systems are built on the cultural premise of using fixed requirements, with not enough thought or attention being paid to systems abilities to deviate from these requirements. Secondly, systems do not generally cope well with adapting to unpredictable change arising from outside of the organisations environment. Over the recent past, different paradigms, approaches and methods have attempted to make software development more predictable, controllable and adaptable, however, the benefits of such measures in relation to the maintenance dilemma have been limited. The concept of flexible systems that are able to cope with such change in an efficient manner is currently an objective that few can claim to have realised successfully. The primary focus of the thesis was to examine WIS post-development change in order to empirically substantiate and understand the nature of the maintenance phase. This was done with the intention to determine exactly ‘where’ and ‘how’ flexibility could be targeted to address these changes. This study uses an emergent analytical approach to identify and catalogue the nature of change occurring within WIS maintenance. However, the research framework design underwent a significant revision as the initial results indicated that a greater emphasis and refocus was required to achieve the research objective. To study WIS’s in an appropriate and detailed context, a single case study was conducted in a web development software house. In total the case study approach was used to collect empirical evidence from four projects that investigated post-development change requests in order to identify areas of the system susceptible to change. The maintenance phases of three WIS projects were considered in-depth, resulting in the collection of over four hundred change requests. The fourth project served as a validation case. The results are presented and the findings are used to identify key trends and characteristics that depict WIS maintenance change. The analytical information derived from the change requests is consolidated and shown diagrammatically for the key areas of change using profile models developed in this thesis. Based on the results, the thesis concludes and contributes to the ongoing debate that there is a discernable difference when considering WIS maintenance change compared to that of traditional IS maintenance. The detailed characteristics displayed in the profile models are then used to map specific flexibility criteria that ultimately are required to facilitate change. This is achieved using the Flexibility Matrix of Change (FMoC) tool which was developed within the remit of this research. This tool is a qualitative measurement scheme that aligns WIS maintenance changes to a reciprocal flexibility attribute. Thus, the wider aim of this thesis is to also expand the awareness of flexibility and its importance as a key component of the WIS lifecycle.EThOS - Electronic Theses Online ServiceGBUnited Kingdo