The current research study conducts an investigation of the dynamic relationship between three key variables: assistive technology (AT) provision, self-determination (SD), and employment outcomes (EOs) as they pertain to persons with disabilities (PwDs) in Saudi Arabia (KSA). The main objective of the study is to investigate the function of AT in improving EOs for PwDs and contextualize the mediating effect of SD on the observed relationship. The study features a quantitative study design which utilizes survey data obtained from a sample size of 120 PwDs. The study participants are employed in either private or public sector organizations situated in Riyadh and Al-Jouf regions of KSA. The conducted survey provides measurements, using a Likert scale, for AT provision, various aspects of SD (decision-making autonomy, self-belief, self-advocacy, goal setting, and persistence and resilience), and EOs (job placement, satisfaction, retention, income level, and career advancement). For data analysis, the study utilizes the partial least square-structural equation modeling. The study findings demonstrate significant direct and indirect effects of AT provision on EOs for PwDs—with SD playing a key mediating role. Specifically, positive effects of AT can be observed in job placement, satisfaction, income level, retention, and career advancements—SD is observed as a key facilitator of AT adoption and effectiveness (EFF) within workplace settings. The findings emphasize the key role of AT investment (accessibility and EFF) in the enhancement of the SD skills of PwDs, and the resulting effect of more inclusive workplace environments for PwDs in KSA.