Over ten years of e-Government and foresight companionship have produced interesting views, proposals and debates. In a first chapter, we will claim that key stakes, however, are no so much how we can head to better e-Gov formulas for the future, but how to think about it. Conventional tools may do the work, but provided they are inserted into a dynamic open-ended perspective where foresight is not just servicing mainstream thinking. In the second chapter, we will examine how past studies have contributed to configure a stimulating learning pathway, gradually enhancing the way e-Gov foresight is envisaged and tied with concrete choice-making and policy relevance. In the third chapter, we sort out the key pending issues that need to be absolutely addressed as part of the e-Gov debate in the coming years, with blueprint provisions to go ahead in this domain, and we conclude by emphasizing the challenges to be coped with, small and large, technical and political, that will eventually make a difference.