An ongoing question amid the pandemic is whether and under what circumstances employees may receive multiple rounds of paid leave under New York’s COVID-19 leave law (the COVID Law). On January 20, 2021, the New York State Department of Labor issued guidance on this issue, which also creates a new obligation for employers. Specifically, the guidance provides that employees are entitled to up to three rounds of paid sick leave under the COVID Law if (i) an employee continues to test positive for COVID-19 after completing an initial quarantine or isolation period, or (ii) an employee returns to work and subsequently tests positive for COVID-19. Under both scenarios, the employee’s positive test triggers a new period of isolation and a new round of paid sick leave. The guidance further instructs that if an employer requires an employee who is not otherwise subject to an order of quarantine or isolation to remain out of work due to exposure or potential exposure to COVID-19, the employer must continue to pay the employee until the employer permits the employee to return to work, or until the employee becomes subject to an order of quarantine or isolation, at which time the employee would be eligible for paid sick leave under the COVID Law. Employers should promptly align their COVID-19-related leave practices with these newly issued clarifications.