Technological advance of the last decades created an atmosphere in which the organizations are forced to look actively for new options for the cost reduction, in addition to, simultaneously, seeking to compete more effectively in their markets. This context requires focused, swift, more flexible and more competitive organizations which are forced, many times, to implement radical changes in the way they conduct business, employ people and use technology. Despite the recognition and the attention given to electronic business (or e-business) over the last years, this type of business hasn’t yet achieved a desirable maturity stage. This problem, current and stated over the last years, demands research efforts so that a solution can be found to solve it. In this chapter, the authors explore a range of constraints which are suggested by the literature to influence e-business evolution, so that organizations could be better equipped in anticipating any difficulties while in progress through their e-business initiatives.