In Europe, large numbers of people with disabilities are willing to work but have problems finding a job. One of the barriers to this is job complexity, particularly for those with low education, low IQ, or cognitive impairments. Digital technologies might help. Specifically, cognitive support technology (CST) has the potential to make jobs less complex and thus more accessible. CST may concern step-by-step digital instructions presented with monitors, tablets, smart phones, beamer projections, or near-eye displays. Based on cross-case evaluations, we aimed to define the success factors in the process of technology selection, development, and implementation. Four cases, situated at public social firms which offer jobs to people with disabilities, were selected. In each case, the optimal form of CST was selected. A qualitative analysis of subjective experiences of work accessibility, performance, usability, and acceptance was applied. The results were positive for most participants in most cases. Once installed, the CST was successful in simplifying jobs. A proportion of the workforce for which a specific job had been considered too complex was able to perform that job when supported by CST. Moreover, a majority of people judged the usability of the technology positively. For the consecutive steps of selection, development, and implementation, we ended up with eleven factors of success; these included, among others, shared and transparent decision making (in technology selection), the iterative and active involvement of workers to optimally adjust work instructions (in technology development), and explicit attention for psychosocial barriers (in technology implementation).