The global pandemic crisis brought on by COVID-19 has prompted a massive scale of implementation of WFH and increased the usage of digital technology due to the movement control order (MCO) enforced by the government. Digitally mature organisations have adapted better to the disruption caused by COVID-19, but this is not the case for organisations that are still stumbling their way through the use of digital technology. The existing research has not delved enough into analysing the influence that digitalisation and working from home have on the culture of organisations, which may alter how employees behave; this continues to be an open question. This study's primary objectives are to investigate the challenges that WFH and digital transformation framed in the midst of the COVID-19 pandemic crisis and to investigate how these challenges have impacted the organisational culture in Malaysia. A structured interview was conducted to reveal that there were overlapping challenges between WFH and digital transformation. The use of technology is intricately bound up with WFH, and WFH is the key factor that has fueled digital transformation throughout the pandemic crisis. Although WFH might be the answer to the problem of business continuity, it still has its drawbacks that might hinder the efficiency of workers and be detrimental to their health. Another major finding is that the introduction of digitalisation and WFH has caused a change in the culture of the workplace. As a consequence, the organisation has become more result-oriented, with an increased focus placed on completing tasks and achieving performance goals.