The Covid-19 pandemic has amplified existing social, economic and political disparities and has brought to the forefront how these inequalities disproportionately impact upon the lives and lived experiences of Indigenous, Black and racialized groups in Canadian society, as is evident through the Twitter hashtags #LandBack, #DefundThePolice and #StopAsianHate. During the 2020/2021 academic year, higher education institutions in Canada pivoted to remote delivery and online learning with the expectation that ‘all things being equal’, learners could engage ‘on equal terms’ in the digital classroom, despite substantial scholarship demonstrating that technologies reinforce existing social disparities. How do instructors create a safe digital environment to understand these apparent contradictions, and facilitate learners in critically examining the structures, relationships and institutions through which digital data, tools and technologies are made and used in society to promote a nuanced understanding of in-real-life rallies on pressing social concerns? This paper will discuss lived-experiences of two racialized women professors in responding to these challenges through digital technologies, and classroom activities and assignments such as analyzing Twitter and publicly-available tweets on the hashtags #LandBack and #DefundThePolice.