This paper explores the evolving dynamics of offensive security operations within organizations, particularly focusing on the strategic decision between insourcing and outsourcing these critical functions. As the field of offensive security matures and becomes commoditized, organizations face a pivotal decision regarding the optimal structure of their security operations to maximize value, efficacy, and strategic alignment. This study examines four primary dimensions that influence organizational decision-making: the quality of security work, integration of the security team within the organizational structure, strategic alignment with long-term goals, and overall cost-effectiveness. By analyzing academic theories, industry reports, and case studies, this paper provides a detailed comparative analysis of insourcing versus outsourcing, highlighting the benefits and limitations of each approach. It also addresses general challenges in security operations such as communication, data sensitivity, and cost, while discussing the shift towards in-house capabilities in recent years. The findings suggest that while outsourcing offers benefits like specialized knowledge and compliance with regulatory standards, insourcing can significantly enhance the quality of security assessments and foster stronger integration with long-term strategic goals. The paper concludes by advocating for a nuanced approach, recommending that organizations may benefit from a hybrid model that leverages the strengths of both insourcing and outsourcing, tailored to their specific needs and circumstances.