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This paper extends earlier research on student facing staff at an emerging Hispanic Serving Institution (HSI) by centering middle management which includes directors, assistant directors, and associate directors who occupy a contested space between executive leaders and frontline staff. Drawing on qualitative interviews, the study examines how these leaders navigate HSI transition amid the loss of federal HSI funding and heightened political attacks on DEI and racial equity. Guided by Critical Race Leadership and LatCrit, the analysis highlights how whiteness and racialized organizational logics constrain middle managers, while also revealing the potential of allyship as resistance. Middle managers who work in solidarity with colleagues at all levels, learn from staff expertise, and stand alongside students emerge as the most powerful actors in sustaining servingness. This requires identifying and dismantling personal bias, reorganizing leadership approaches, finding courage in the face of administrative discontent, and refusing to tolerate harassment or harm by addressing it directly. This session is a call to action for middle managers across HSIs. The charge is to reject passive compliance, resist superficial equity, and lead with courage. Authentic servingness depends on middle managers embracing resistance as their leadership practice.