The purpose of this chapter is to examine if and how e-government is being addressed in a holistic manner across levels of in a federalist jurisdiction such as Canada—and that of Italy which is progressively moving towards federalism. Conceptually, there are tensions between the technologically driven vision of “federated architectures”—a term which implies co-ordination and balance between centralised and devolved governance mechanisms (enjoined in some manner), and the term “federation” in a political sense—implying formal separation and autonomy between government levels. This chapter compares Italy and Canada since both have been witness to ongoing discussions around political federalism in recent years. Some comparative lessons are identified in terms of interactions and interrelations between levels of government in a more digitally and socially interdependent world.