This study examines the complexities of offshore outsourcing undertaken by important corporations in Singapore and Indonesia, whereby they engage in subcontracting their activities to Business Process Outsourcing (BPO) firms located in India and Bangladesh. The objective of this study is to comprehensively examine the various factors that drive, shape, and impact the strategic decision-making process. This study utilises a content analysis approach to thoroughly examine textual data obtained from annual reports, press announcements, business statements, and industry publications. This systematic approach facilitates the provision of qualitative insights pertaining to the determinants of offshore outsourcing decisions, hence contributing to a thorough comprehension of the complex offshore outsourcing environment. The primary conclusions of this study highlight the prevailing rationale behind offshore outsourcing, which is the pursuit of cost effectiveness. Prominent corporations place a high emphasis on the reduction of operational expenses by leveraging the cost advantages associated with lower labour prices in India and Bangladesh. Concurrently, they endeavour to get entry to a proficient pool of talent, acknowledging the presence of specialised talents and domain expertise within certain geographical areas. Additionally, the study emphasises the growing tendency to prioritise core capabilities, resulting in improved productivity and operational efficiency. Furthermore, there is a growing emphasis on the implementation of efficient business continuity planning and risk mitigation techniques, which serve as crucial measures to counteract unexpected interruptions by offering geographic diversity and redundancy. The firms employ many tactics in offshore outsourcing that involve cost optimisation, talent recruiting, risk management, and quality control. Notwithstanding the benefits, overseas outsourcing poses various problems, encompassing cultural and linguistic hurdles, ongoing quality control and data security apprehensions, as well as intricate legal and ethical deliberations. The future implications underscore the need for a balanced approach that effectively reconciles considerations of both cost and quality. In order to effectively navigate the intricate offshore outsourcing landscape, it is advisable to employ strategies that handle cultural and language obstacles, as well as demonstrate vigilance in resolving compliance and ethical problems. This study provides practical recommendations for organisations, while also acknowledging its limitations, particularly the reliance on textual data analysis, which may not fully capture real-time nuances. This study highlights the wider economic and social consequences associated with offshore outsourcing choices, which have an impact on employment markets and corporate strategies in both the nations that outsource and those who receive the outsourced work. This research makes a valuable contribution to the current knowledge of offshore outsourcing by highlighting its varied nature within the context of the global business landscape.