This study raises the radical questions on the nature of e-Learning in order to implement e-Learning strategy which is linked to the e-Learning vision. The five major issues are on the question in order to explore e-Learning from the different perspectives. The first question is about what is e-Learning and kinds of learning activities in e-Learning. The nature and attributes of e-Learning are explained in terms of digital learning environments and the concept of learning, resulting in the major features and differences from other approaches to learning including learning activities in the context of off-line. The second question is related to the potentiality to make meaningful learning through e-Learning. Most of e-Learning, in a sense, is not considered to be \'learning\' but e-Training. The third question is about management issues of e-Learning. The learning itself cannot be managed through the lens of the nature of learning. Learning is a kind of self-regulated and self-influential activity. The concept of learning cannot be harmonized with the concept of management. The concern of the fourth question is on contextuality of e-Learning. The process of learning should be contextualized in which learning is happening. However, digitalization of information for e-Learning means that there are little chance to contextualize learning in e-Learning. The final question goes with the issues related to efficiency, effectiveness, and meaningfulness of e-Learning. The dilemma between efficiency and effectiveness are tackled in terms of the issues of meaningfulness of e-Learning. This study ends up with several research issues such as the social life of information from the perspectives of learning ecology, types of knowledge creation with social capital and community of practices, the limitations of learning objects, and storytelling as one of the ways of processing contents.