The use of telehomecare has the potential to facilitate access to healthcare services for vulnerable populations. However, evidence on the implications of telehomecare on various aspects related to patients, healthcare professionals, organizations, and healthcare systems is still limited. Assessing the various effects of telehomecare for these different groups of stakeholders is thus an essential step to ensure future integration of this technology into mainstream healthcare services. A synthesis of lessons learned from the evaluation of three telehomecare experimentations targeting specific vulnerable groups is proposed. This paper presents the various models that were implemented to assess telehomecare services for vulnerable populations, explores issues related to conducing telehomecare evaluations, and provides a reflection on key factors that might influence the success of telehomecare projects. Lessons learned from these three experimentations provide valuable insights to orient the development of telehomecare services for various vulnerable groups in the population.