The latest advances in information technologies have fostered more innovative Telemedicine systems that provide high-quality medical screening and diagnostics to patients anytime, anywhere. These new developments have drawn significant attention, especially in underserved communities as well as during crises and emergencies. However, in order to successfully implement these technologies and provide adequate care, various challenges need to be tackled. For instance, networking techniques must be improved to optimize bandwidth, frequency, and data transmission. In addition, these technologies must implement robust security features in order to maintain patients’ privacy. Throughout this chapter, the authors present recent developments in Telemedicine and provide a detailed taxonomy to classify the different components forming Telemedicine. Additionally, we investigate the challenges in designing effective Telemedicine systems for all types of users. Furthermore, we highlight a holistic view that can guide the future development and design of Telemedicine systems, enhancing the user experience of both patients and healthcare providers. This research effort suggests the need for systematic perspectives to enhance the current Telemedicine systems with regards to models, frameworks, guidelines, and management decision-making processes. Nevertheless, several challenges respect to design strategies, communication management, reliability, availability, and maintainability still exist.