Despite rising participation rates in Portugal, a gap persists between general and vocational upper secondary students' transition to higher education (HE). This study employs a qualitative methodology, specifically through content analysis of focus group discussions, to explore the factors influencing vocational students' reluctance towards higher education, amidst specific policies designed to aid their transition. Empirical findings suggest that vocational students may exhibit reservations stemming from self-perceived academic deficiencies, impacting their self-confidence in continuing their education at a HE level. Nevertheless, confidence in market-valued practical skills might motivate HE consideration within a vocational domain. Their practical focus also makes HE seem less immediately applicable in the labour market. Many prioritise integration into the workforce for short-run objectives, seeking breaks, experience and financial earnings. Aiming for earning and practicality, many lean towards the labour market over HE, even considering emigrating to achieve financial stability. The study emphasises the need for Portuguese educational policies to align vocational training with HE, supporting diverse student ambitions and holistic career paths.