A growing body of evidence has been assembled in recent years indicating the influence that early educational experiences can have on a young person's prospects of progressing to university. These include experiences associated with the transition to post-16 study, which can also involve a move to a different educational institution. Whilst applicable to young people from wide range backgrounds, navigating the post-16 education system, and having the knowledge and confidence to advance through it, can be more challenging for those from backgrounds with limited experience of post-compulsory education. However, the nature of the challenges to post-16 educational progression faced by those from widening participation backgrounds, as well as what works and what is needed, remain comparatively under-researched. Moreover, evidence suggests that the disruptions to education wrought by the pandemic may have exacerbated and added to established challenges. This article reports on the findings from an investigation that sought to better understand these issues and how they might be addressed by hearing from those most directly impacted: the young people outreach initiatives seek to support.