The majority of Canadians agree they have the right to end-of-life care in their own homes. While a palliative approach to care in the home setting has been demonstrated to be beneficial for patients and the healthcare system, it has rarely been well-integrated through an eHealth approach. Thus, in 2018, we piloted the RELIEF app, a digital symptom self-reporting tool for patients with palliative care needs. This was followed by the initiation of an extension phase of RELIEF in the home care setting. In this commentary, we share the implementation perspectives and experiences of the researchers and healthcare workers involved in this home care phase. It was mainly expressed that there were challenges with nurses feeling involved, supporting the research program, and using the technology, while patients and family caregivers had challenges using the app and cooperating with staff. We describe our lessons learned from these experiences and future changes to be enacted. A detailed report of this trial will be made available in future publications.