In 2019, a decline in apprenticeship starts prompted the London Borough of Hounslow to make an apprenticeship pledge in its Corporate Plan 2019-2024, committing to create 4,000 new apprenticeships and training opportunities to help young people into work. This article investigates experiences of young apprentices in Hounslow before and during the COVID-19 pandemic. Exploring the perspectives of two apprentices, two employers and one training provider in a small-scale qualitative study, the authors identify key hindering and supporting factors affecting entry into and sustainability of apprenticeships, and progression towards professional employment. They found that labour market entry was intensely hindered by competition (with peers who had better maths and English qualifications, for a small number of apprenticeships) and organisational barriers (such as managers with prejudices against young people, stigmatising apprentices and apprenticeships). Supportive factors identified include personal characteristics (such as a positive mindset, enabling young people to persevere despite a disadvantaged socioeconomic background and lack of family support, for example) and supportive relationships (e.g. mentoring) between apprentices and their training providers or employers.