Background/Context: In the United States, American Indian youth face multiple forms of marginalization in a settler-colonial school system. In particular, exclusionary school discipline practices (e.g., out-of-school suspensions, expulsions) have been used as tools of exclusion, through which Indigenous bodies are erased from the learning spaces while reinforcing and perpetuating white settler-colonial privilege. To combat settler-colonial violence deployed through disciplinary policies and practices, the Indigenous Learning Lab intervention was implemented in a rural Midwestern high school from 2019 to 2024. The Indigenous Learning Lab is a community-driven participatory design process aimed at systemic transformation. Despite the co-development of locally meaningful solutions through the Learning Lab methodology to tackle racialized school discipline, the disruptions caused by the dual pandemics of COVID-19 and racial unrest required situated adaptations in response to the constantly shifting local sociocultural and political contexts. Purpose/Objective/Research Question/Focus of Study: This article examines how Indigenous youth, families, and educators as well as non-Indigenous professionals engaged in collective speculative future-making during the implementation of transformative solutions by navigating uncertainties and political tensions induced by the dual pandemic in order to restructure the present oppressive learning environment, with the political goal of disrupting the settler-colonial punitive school system. To understand the role of future-forward speculations in transforming a punitive school system within the complex, politicized settler-colonial context, we utilize three dimensions of speculation--historical, sociocultural, and sociopolitical--as our guiding theoretical framework. Research Design: To examine collective speculative future-making led by a rural high school community, this instrumental case study employs an abductive approach to analyze video-recorded implementation team meetings, individual or focus group interviews, field notes, and artifacts collected throughout the 2021-2022 academic year. During this period, the school community began implementing the new behavioral support system designed by local stakeholders (e.g., Indigenous students, educators, families, and community members) through the Learning Lab process to address racialized school discipline. Conclusions/Recommendations: The Northwoods High School community engaged in collective speculative future-making to dismantle the oppressive, settler-colonial school system. Through historical, sociocultural, and sociopolitical speculations, the school community critically interrogated often-taken-for-granted present systems, policies, tools, practices, and identities and collectively reimagined possible futures by developing alternative and liberatory stories and sociopolitical relations. By participating in a collective struggle toward possible futures, the local school community can engage in speculative dreaming to refine and consolidate a new school system centered on joy, dignity, and prosperity for students from nondominant communities.