Dentistry is an entrepreneurially oriented public interest profession that must maintain a balance between professional specificity and business sustainability. Communicating with patients is vital in a competitive system, and the dentist needs to use handy resources such as websites and social media. The aim of this research is (a) to examine whether websites and social networks are a digital entrepreneurship tool used in the dentistry profession in Oradea, a city in full economic development in Romania, to promote the profession nationally and internationally, (b) to compare the changes made using digital tools in the period between 2018–2021 for all licensed dentists in the mentioned city (between 430–450 people, depending on the stage of analysis) using the content analysis method and (c) to identify how the lockdown period imposed by the emergence of the COVID-19 pandemic influenced not only the sustainability of the medical services provided to the population but also the communication practices of the dental offices. The results of examining the dentist’s online presence reveal that there is an interest among practitioners to grow their business sustainably through a digital presence that is increasingly relevant to them and their clients, but the potential remains under-exploited.