This paper discusses the implications of policy design and administration due to digital transformation in the social security system of Jordan. Under the increasing integration of modern technologies, it is also determined how digital tools would further provide more effective, inclusive, and accessible social security services. In providing an adequate account of the benefits and challenges of digital transformation at the doors of the National Social Security Corporation (NSSC), a mixed-methods approach was adopted that involved quantitative surveys, in-depth interviews, and document analysis. Therefore, this study proves that high levels of technological innovation should be practiced with low levels of equity, inclusion, and social protection principles. Additionally, there is a call for wide regulatory frameworks covering data privacy issues, system integration, and all types of human participation in automated interventions. This is demonstrated by the findings that successful digital transformation requires policies to be evaluated on an ongoing basis, improved interdepartmental cooperation, and investment in digital literacy. It underlines the importance of ensuring that digital transformation efforts meet the needs of society so that this modernization will benefit everyone, especially the most marginalized, with greater and better public services.