The explosion of e-commerce creates new opportunities for courier companies to thrive, making the industry one of the success stories, due to its sustainability and resilience during the pandemic. As customers become more familiar with COVID-19, they adopt new online purchasing behaviors toward branding preferences. The purpose of this paper is to analyze the impact of risk familiarization on courier companies' digital branding. This paper investigates the application of the psychometric paradigm by Fischhoff ho suggested risk novelty as a key factor for the level of risk perception. Five big companies with global trading activities were selected and analyzed on a three-period time: the year before, the first year, and the second year of the COVID-19 pandemic, by using passive crowdsourcing data. The results indicate that after the first year of the pandemic, online customers' risk perception of COVID-19 hazards decreased, and consumers returned to their pre-COVID-19 behavior regarding brand preference. However, the dramatic escalation of new infections caused by new COVID-19 mutations reversed their online purchasing attitude from non-branded to branded preferences. The outcomes of the research can be used by scientists and supply chain risk managers to redefine risk mitigation strategies, COVID-related information marketing strategies and innovation investments within the industry. The research further introduces dynamic simulation modeling to be used as a risk management tool in favor of courier companies' proper resource allocation and digital optimization.