This dissertation’s central ambitions are to point out and illustrate how design-oriented information systems research (ISR) can be utilized for critical and emancipatory (C&E) purposes as well as—although to a lesser extent—to offer a considerably different perspective on how ISR can contribute to the sustainable development (SD) research agenda. Research programs intending to remove entrenched inequalities by changing the status quo exhibit a C&E orientation. A design-oriented methodology tends to be predestinated as underpinning for such endeavors because of its explicitly stated aim of change. The omnipresent SD discussion, at least in its original conceptualization, is one of the most prominent areas where design-oriented research programs with C&E features are urgently needed. In particular, design science research in information systems (DSRIS), the design-oriented research program in ISR, is considered to be a vital ingredient: the design of appropriate technical systems is gaining in importance, because the complexity and dynamics of SD issues exceed human problem-solving capabilities. However, SD concerns cannot be addressed by isolated technical artifacts; technical systems have to be aligned with the social systems in which they are embedded. This broader endeavor is called the design of socio-technical systems. In comparison to research under this heading, DSRIS rarely strives for C&E goals. This curious situation can be traced back to the methodological suggestions given in the hope that they bridge the ‘relevance-rigor gap’: relevant research has to be carried out in response to problems articulated in practice and results have to be rigorously evaluated in practical settings to demonstrate their efficacy to solve the explicated issues. Besides the inherent challenges of both these prescriptions, from the stance of C&E research, it seems implausible that powerful actors would grant access to a setting and support projects that challenge their positions. Hence, the postulated aim of change is merely an euphemism for endeavors that reinforce and solidify the status quo—they, due to the lack of empowering potential, can solely further what Habermas termed the ‘colonization of the lifeworld’. The method for the design of ‘possible worlds’ proposed in the present inquiry not only helps to overcome this limitation, but it simultaneously integrates DSRIS more clearly with the overarching undertaking of devising socio-technical systems. Against this background, a designed `possible world’, seen from an explicated value position, is a more desirable, theoretically possible alternative to factual existing contexts in a particular domain. It functions as ‘crash barrier’ for the design of social systems and it can at the same time be leveraged as domain model from which it is possible to elicit requirements for the construction of a reference architecture that describes technical systems backing the processes of and within the ‘possible world’. However, in addition to the method’s development, the Ph.D. dissertation also illustrates the former’s application by designing a reference architecture for systems that support the decision-making processes of community-driven sustainable human development initiatives; one at least theoretically possible concretization of SD. As such, the inquiry makes three research contributions: its primary focus is a constructive extension of the disciplinary body of knowledge through the methodical guidance for C&E DSRIS; however, the reflection of SD as part of the exemplary application is also a critique of the way SD issues are currently tackled and of how they are integrated into the ISR canon. To realize these aims the study proceeds as follows: based on a critical reflection of the philosophical underpinnings of DSRIS, it explicates different routes to bridge the relevance-rigor gap. One of these avenues then serves as starting point for the construction of a method that specifically addresses the peculiarities of C&E DSRIS. The core derivation from the traditional conceptualization of design-oriented ISR lies within the sketch of a desirable, hypothetical alternative of factually existing social systems, which, through the contrasting with the latter, allows to carve out intervention entry points, i.e., aspects in which the ‘factual world’ has to change to become more like the ‘possible world’. To justify the claim that this transition, manifesting itself in the determined intervention entry points, is at least theoretically possible and not utopian, the ‘realist synthesis’ as a technique for the gathering of justificatory evidence from the existing body of knowledge is presented. Rooting endeavors of DSRIS in the scientific knowledge base is an important move to free them from being confined to those problems that are articulated by powerful gatekeepers in practical settings. However, for the design of ‘possible worlds’ to bear fruit in ISR, this step needs to be complemented. Therefore, the synthesis is adapted to also permit the extraction of, from the perspective of the underpinning normative stance, suitable ‘draft meanings’, because these progressive (social) structures or organizational options resulting from interventions provide the basis for the design of reference architectures that are aligned with the ‘possible world’. To illustrate this, from an ISR perspective, fundamental usage scenario, the inquiry, based on a devised preliminary reference architecture development approach, carries out the afore-mentioned exemplary application of the method for the design of ‘possible worlds’.