The COVID-19 pandemic has created additional complexity for employer considerations during the festive season, particularly at the cusp of what seems to be the dreaded “second wave”. Many employees have exhausted their annual leave due to COVID-19 related company closures or in instances where their sick leave entitlement was exhausted. Are employees entitled to take unpaid leave for holiday purposes where their annual leave is exhausted? Does an employer have to pay an employee who is in quarantine after returning from a “hotspot” area over the festive season? The purpose of this guide is to assist you in navigating potential employee related challenges in the upcoming “COVID-19” holiday season and in the new way of work commencing in 2021.