Many eHealth initiatives are never implemented or merely end as pilot projects. Previous studies report that organisational, technical and human issues need to be properly taken into consideration if such initiatives are to be successful. The aim of this paper is to explore whether previously identified challenges within the area have remained in the Swedish eHealth setting or whether they have changed. After interviewing experts in eHealth, we present a classification of areas of concern. Recurrence of previously identified challenges was found, but also new issues were identified. The results of the study indicate that there is a need to consider organisational and semantic issues on both national and international levels. Legal and technical challenges still exist but it seems even more important to support eHealth initiatives financially, increase practitioners knowledge in health informatics and manage new expectations from patients.