There is an ever increasing number of people with Long Term Conditions for which telehomecare is being promoted to offer support. In this emerging area little attention has been given to the barriers and challenges faced when introducing such systems. Yet it is important to avoid known pitfalls as well as building upon known successes. This chapter discusses barriers often encountered with particular attention given to lessons categorized under the following headings.(1) Structural – determining whether telehomecare should be embraced; (2) Implementation – obstacles experienced when implementing telehomecare, (3) Adoption – difficulties translating small scale initiatives to mainstream service delivery. In so doing, we trust initiatives prove to be more ‘successful’, better health care is delivered, and a more accurate and reliable evidence base is generated.