The dynamic nature of IS alignment has been recognised in literature, nevertheless most empirical studies still focus on the relationships between business and IS at strategic level. Building on previously identified IS alignment factors (IT governance, IT value, communication, partnership, scope and architecture, human resources skills) this study incorporates an empirical investigation in a large insurance organisation that examines the relationships between business and IS across different organisational levels. By measuring the level of IS alignment of five strategic projects the impact of the factors affecting IS alignment is analysed. As previously reported IT governance was found to be the most relevant factor when high levels of IS alignment are obtained. However, by examining the variations of IS alignment for each project common areas of low IS alignment were identified: understanding of IT by business, balance metrics, budgetary control and share goals, risk and rewards. Findings reveal organisational structure and the business perception of IT value as the root causes behind low levels of IS alignment within those areas. Additionally, results exhibit a bigger IS alignment gap between the perceptions across strategic, tactical and operational levels than the traditional gap between business and IS.