The COVID-19 pandemic continues to affect prisons internationally. Existing research focuses on infection data, meaning we do not fully understand how COVID-19 shapes frontline prison dynamics. We draw on qualitative interviews with 21 Canadian federal correctional officers, exploring how the pandemic impacted prison management. Officers suggested inconsistent messaging around COVID-19 protocols reduced institutional and officers' self-legitimacy, fracturing trust relationships with incarcerated people. Furthermore, officers suggest that personal protective equipment such as gowns and face shields took on multiple meanings. We use Lévi-Strauss' floating signifier concept to analyse how individual definitions of 'safety' informed day-to-day prison routines. We conclude by arguing that legitimacy deficits and contested definitions of 'safety' will continue to create uncertainty, impacting prison operations going forward.