Digital citizens have been using online synchronous communications (OSCs)-based milieus since the last decade. OSCs can provide these online communities with new and challenging opportunities via instant interactions, which are OSCs’ dominant nature, in lifelong learning. OSCs, therefore, help online learners, as lifelong learners, and communication workers (online communication designers, media coordinators, online managers, technology-support staff, multimedia designers, etc.) understand this milieu better to have more benefits. In this study, media richness theory and four cultural issues (biases, stereotypes, ethics and values) are discussed together to highlight the communicational characters of the OSCs. To utilize the communicational prospects of OSCs, this communication theory provides communication workers with useful guidelines related to cultural issues, which expand on future directions for OSCs. Finally, the researchers develop a framework according to the strategies of media richness theory, which declares that there must be a fit between technology and communication structures to reduce task-related ambiguity.