This paper analyzes two challenges of Internet evolution by evaluating the dynamics of change against the outstanding aspects of the current situation. To understand these challenges, a model that exposes the factors that drive the dynamics of Internet evolution is discussed first. The conclusion drawn is that attitude and technology are the two vectors that lead the evolution of Internet. Secondly, the contemporary context with regard to technology development and information society attitudes is analyzed. Finally, it is concluded that the necessity of a paradigm shift in the attitude of organizations and the threat of unsustainable technology development are two of the main challenges towards the future Internet.