Whilst universities across the global community had adopted new digital learning standards prior to COVID-19, the radical effect of quarantines and social distancing on remote learning needs has fundamentally altered the structure of modern English as a second language (ESL) education in higher education institutions. The current investigation critically explores the educational paradigm from a perspective of content dissemination, learning best practices, and knowledge acquisition in Hong Kong colleges and universities. Through a critical review of the literature surrounding digital learning challenges and opportunities, evidence revealed an overlapping proposition of adaptation and discipline which many students lacked prior to the COVID-19 interruption. By comparing the perspectives of 1062 students across ESL programmes taking English for academic purposes (EAP) and English for specific purposes (ESP) courses within several Hong Kong institutions, this study has confirmed the potential advantages of digital learning solutions including time management, self-paced learning, and knowledge engagement. Students were surveyed using a digital, structured questionnaire to capture a robust representation of experiences during the COVID-19 pandemic and their effects on student learning outcomes. Through quantitative analysis, student feedback has confirmed several developmental challenges related to skills gaps, personal discipline, environmental forces, and student learning expectations. Based upon these findings, a revised protocol for digital citizenship has been proposed which focuses on core principles of self-accountability and discipline that evolve out of proactive, motivated learning objectives that link students to their digital identity and role. Ultimately, these observations indicate a need for future assessment of the competing motivations shaping student engagement in digital learning services and traditional classroom offerings as the COVID-19 pandemic restrictions are lifted and the educational industry evolves towards its new normal.