 The study aims to explore cultural factors related to patients and their caregivers that have influenced the pilot implementation of a connected health program in the home health care department at King Saud University Medical City, Riyadh, Saudi Arabia. The results revealed two categories, culture-related factors including language and communication, cultural views on using cameras during consultation, non-adherence to web-based consultations, and family role and commitment, and caregiver characteristics in telemedicine that includes their skills and education and electronic literacy. The study recommends exploring the use of interpreters in digital health, creating awareness among the local population regarding privacy in digital health, and actively involving direct family members with the health care providers. This article was authored by Abdul Aziz A. Al-Odani, Marwa Mazin Hasuna, Fatima Arkadri, and others.