This chapter uses information theory to study the effect of the Internet and e-business over the digital divide. It develops a framework that defines four types of information technologies and Internets based on four dimensions of information: physical, syntactic, semantic, and pragmatic. Technologies like e-mail that only make use of the first three hardly interact with the industrial infrastructure and superstructure. Nonetheless, technologies like e-commerce that require the pragmatic dimension, which is related to matter and energy (products and services) need such structures. For example, e-commerce requires a trustworthy transportation and payment infrastructure. Unfortunately, developing countries are lacking them. This differential capacity to use the pragmatic dimension of AdvIT/IS (pragmatic fragility) explains why developing countries are not able to skip industrialization and jump into the information era. This pragmatic fragility increases the existing digital divide since implementing e-business in developing countries ends up being the digitalization of bad business practices.