This manuscript details a critical reflection on how Design Science Research (DSR) was applied to the guided development and implementation of a strategy formulation process for a civic tech project called MobiSAM, which was executed in a marginalized local government context. It also demonstrates how the application of DSR is augmented by Soft Systems Methodology (SSM), to ensure that the unstructured properties typically present in multi-stakeholder deliberation (required in civic tech project strategizing) are accounted for in the strategy formulation exercise. To underpin this critical reflection on the emergence and application of the civic tech project strategy framework (the artifact), pragmatist interpretivism is employed. This qualitative paradigm underpinning the critical reflection supports better understanding of strategy related challenges primarily through participant observation and interviews with actors in the civic tech context. The findings reveal that for an unstructured problem like civic tech project strategizing, SSM is particularly instrumental to the application of four DSR guidelines, namely-problem relevance, design evaluation, research contribution and communication of DSR.