This research aims to explore the status effects of the Sudden, and gradual of AI-Driven Cyber Security (AIDC), Big data analytics and Business Intelligence (BI) The strategic flexibility (SF) and entrepreneurship (ENT) on Iraqi internet services providers ISPs. The work fills an important lacunae in what the advanced dimensions of technology have with regard to its influencing both SF and ENT outcomes in developing economy context, where empirical evidences are scant. A cross-sectional survey based on a quantitative research methodology was conducted on 113 professionals in Iraqi telecommunication sector. A partial least squares structural equation modeling (PLS-SEM) approach was adopted to examine 10 hypotheses concerning the relationships between technology capabilities and SF and ENT. The results reveal the in-depth direct influences of AIDC, BDAC and BI on the SF and ENT factors. SF is found to be an important mediating factor that significantly strengthens the influence of technological competence on ENT outcomes. This indicates two paths (direct and indirect) to reach SF and ENT, facilitated by AT. The present study also extends the literature by adding further empirical evidence from Iraq which indicates that integrating AIDC, BDAC and BI has a synergetic impact on SF but also on ENT. The findings apply only to the Iraqi context in geographical terms. The results show that spending on these technologies are strategic spending rather than operational expenditure. “Institutions should structure responses that are flexible to fit in with people and things, in order to harness the maximum benefit from technology.” These capabilities may be viewed as bases of competitive advantage (CA). This study is first of its kind in Iraq which examines the synergistic effect of AIDC, BDAC and BI on OSC and ENT performance where insight into developing economy perspective becomes present.