Recent studies show that more than half of Saudi Arabian (SA) organisations fail to realise business benefits from their IS investments. This has been largely attributed to the contextual misalignment between information technologies and the needs of developing countries. In the IS literature on benefits realisation, the application of benefits dependency networks (BDN), have been established as being helpful in improving IS projects outcomes. This research investigates current IT development practice in SMEs in Saudi Arabia and reports on some of the challenges that these businesses need to overcome to achieve benefits from their IT investments. Evidence from the literature and a field study suggests that workarounds are widely used when implementing new IT, particularly to facilitate the continuation of embedded cultural practices. The paper argues that integrating the Theory of Workarounds into frameworks for benefits realisation would offer a useful conceptualisation of IT implementation practice to support businesses in developing countries such as Saudi Arabia to improve outcomes when investing in IT.