The selection of a new healthcare information system (HIS) has always been a daunting process for clinicians, health care providers and policy makers. The objective of this study is to present the lessons learned and the main findings from several relevant case studies to support this process. Data were collected by retrospectively reviewing the summative results of three well-established systems, acquiring feedback from two E.U. projects, and conducting semi-structured interviews with a number of collaborators involved in electronic healthcare interventions. Selection issues were identified and classified into the following five categories: (i) data creation, (ii) data management, (iii) data sharing, (iv) data presentation and (v) modules management. A mind map was also structured to provide a more manageable list of issues concerning the most common electronic clinical technologies (e-CT). The vendor manual is intended as an overview of the merchandise e-CT and therefore has limited potential in supporting effectively the selection process of a new HIS. The present classification and the mind map - based on lessons learned - provide a ready-to-use toolkit for supporting the HIS selection process when healthcare organisations are unable to employ research development groups to lay the groundwork for building a new HIS from scratch.