question: Purpose: The purpose of this paper is to share reflections on the frontline delivery of a wrap-around secondary school re-engagement programme on compounding digital inequality during the COVID-19 lockdown Design/methodology/approach: This paper presents a deliberative reflection on practice and policy lessons learned while negotiating the digital divide during the COVID-19 lockdown in the delivery of the yourtown education youth engagement programme Findings: Frontline youth worker practice lessons highlight the compounding effect of digital inequality on vulnerable young people who are already disengaged or disengaging from secondary education and the necessity for a reflexive, agile and adaptable practice response, particularly during unprecedented events such as the COVID-19 pandemic Originality/value: This paper presents a wraparound service perspective and outlines important practice lessons gained from adapting an education re-engagement programme to respond to the COVID-19 lockdown in the Greater Brisbane area, Australia © 2020, Emerald Publishing Limited