Introduction: Employment is a key factor for social inclusion, yet persons with disabilities in Cyprus continue to experience exclusion from the labour market. Barriers such as limited digital skills, poor access to assistive technology, and weak enforcement of reasonable accommodation laws remain common. Aim: This paper investigates the structural and practical barriers faced by persons with disabilities in accessing and sustaining employment in Cyprus, focusing on digital inclusion, assistive technologies and reasonable accommodation. Methodology: A qualitative, exploratory approach was used, combining policy and document analysis, semi-structured interviews with representatives of organizations of persons with disabilities, and quantitative data from employers who completed the European Disability Forum’s questionnaire. Results: The study found low levels of employer awareness regarding disability rights and support frameworks. Only 10% of employers had hired a person with a disability, and most lacked internal policies on digital skills, assistive technology, or reasonable accommodation. These findings align with broader European Union (EU) trends but are intensified in Cyprus by a lack of national coordination. Conclusions: Improving digital training, simplifying assistive technology funding, and strengthening employer engagement are essential for inclusive employment. Comparative practices from other EU countries highlight viable pathways for reform.