This study invites scholars and practitioners to reflect on the digital transformation of retail throughout the year 2020. The COVID-19 pandemic has activated two countervailing forces particularly relevant to the dynamics of the retail sector. On the one hand, months-long lockdown and stay-at-home measures have boosted e-commerce transactions at the expense of brick-and-mortar sales. On the other hand, the pandemic has contributed to economic hardship, and drops in customer confidence and discretionary purchasing. Thus, 2020 has been a year where retailers have had to juggle between handling extraordinary challenges and embracing opportunities via digital innovations. Against this backdrop, we set out to better understand the nature and scale of retail actors' digital responses to the disruptions generated by the pandemic. Because these responses are likely to have been contingent on their socio-cultural and economic setting, we opted for a comparative study of the most salient initiatives in China, France, and Canada. This approach, which highlights the diversity of responses across countries, intends to broaden the spectrum of possibilities for decision-makers across the globe when it comes to leveraging digital technology in the retail sector.