The current technological and social panorama brings current benefits and threats that depend upon skills to conduct and achieve. Cultural digital skill is a call for benefiting from technology, and foremost cultural digital skills are imperative because they grant folks the ability to utilise technology in a transient’s manner. Sierra Leonean universities and technical and vocational institutions endure advancing an Information Communications Technology labour pool that is neither modelled by policy nor well assigned to the industry requirements, exclusively at the great point. The Municipal’s graduates are underprepared to accommodate the appeal of the current organisational structure and are incapable of establishing impressive results, progressing to a dearth of proficient and skilled labour pool appropriate for the Freetown cultural digital revolution. The paper anticipates appraising the foremost cultural digital skills evolvement procedure in higher learning institutions, the social reality of the process, and identifies possible challenges leading to the cultural digital skills gap. The paper utilised an archival research strategy and applied the design social reality gap framework with its optimistic record of social dimensions to appraise curriculum, staff, equipment, student enrollment, laboratory and graduation at the higher learning institutions in Freetown Sierra Leone that teach Information Communications Technology programmes. The research findings communicate that there is a low student enrolment in Information Communication Technology programmes resulting in a low number of graduates joining the municipal industry. The appeal for Information Communications Technology skills continues to expand while the industry complains that graduates are not well prepared to undertake projects from the industry forcing the Freetown municipality to rely on foreign expertise. The curriculum utilised in the learning institutions is mismatched, leading to inappropriate competencies to be evolved among the graduates. In spite of the prevalence of standards and protocols from the university regulator (Sierra Leone Tertiary Education Commission), they are not enthusiastically sanctioned due to challenges faced by the regulator and the institutions. A recommended operation strategy was evolved to bridge Freetown's cultural digital skills gap among government agencies, educators or trainers, and employers. The paper spotlighted skills evolvement in higher learning institutions, excluding the technology hubs and complementary programmes offering training programmes for advanced cultural digital skills in the Freetown Municipality. The paper confirmed that inappropriate competencies are being evolved among the graduates, making them unqualified for meeting the requirement of the industry and the Freetown municipality. The paper responds to the policies related to Information Communications Technology labour pool evolvement in the Freetown municipality. The paper will trigger the evolvement of current thinking or thought and social interactions among the learning institutions, academic staff or trainers, employers and government agencies to link the cultural skills gap leading to an empowered municipality competent of upspringing the economic expansion.