The community of scholars focused on information systems in organizations and society (the IFIP 8.2 community) has grown in number, voice, and influence over the last 25 years. What will this community contribute during the next 25 years? We speculate on two possible areas: more articulate conceptualizations of information systems and more detailed socio-technical theories of their effects. For both of these possibilities, we project forward from the historical trajectory of the IFIP 8.2 community’s involvement. Like all speculative scholarship, our argumentation is more about imagining possible directions than arguing the superiority of one particular view relative to all others. This considered speculation is directed at both stirring the community’s collective mind and advancing the value of this community’s work to interested others.