Artificial intelligence (AI) is recently seeing significant advances in teledermatology (TD), also thanks to the developments that have taken place during the COVID-19 pandemic. In the last two years, there was an important development of studies that focused on opportunities, perspectives, and problems in this field. The topic is very important because the telemedicine and AI applied to dermatology have the opportunity to improve both the quality of healthcare for citizens and the workflow of healthcare professionals. This study conducted an overview on the opportunities, the perspectives, and the problems related to the integration of TD with AI. The methodology of this review, following a standardized checklist, was based on: (I) a search of PubMed and Scopus and (II) an eligibility assessment, using parameters with five levels of score. The outcome highlighted that applications of this integration have been identified in various skin pathologies and in quality control, both ineHealthandmHealth. Many of these applications are based on Apps used by citizens inmHealthfor self-care with new opportunities but also open questions. A generalized enthusiasm has been registered regarding the opportunities and general perspectives on improving the quality of care, optimizing the healthcare processes, minimizing costs, reducing the stress in the healthcare facilities, and in making citizens, now at the center, more satisfied. However, critical issues have emerged related to: (a) the need to improve the process of diffusion of the Apps in the hands of citizens, with better design, validation, standardization, and cybersecurity; (b) the need for better attention paid to medico-legal and ethical issues; and (c) the need for the stabilization of international and national regulations. Targeted agreement initiatives, such as position statements, guidelines, and/or consensus initiatives, are needed to ensure a better result for all, along with the design of both specific plans and shared workflows.